hydrogen fluoride in acetonitrile

Multi-step reaction with 25 steps 1: 1.) dimethyl sulphide, N-chlorosuccinimide, 2.) triethylamine / 1.) toluene, ether, -20 deg C, 2 h, 2.) 30 min2: 63 percent / benzene / 6 h / 80 °C3: 86 percent / ethyl di-isopropylamine / CH2Cl2 / 2 h / Heating4: 70 percent / Dowex 50W X-8 / methanol / 3 h / Ambient temperature5: 95 percent / hydrogen / 10percent Pd-C / methanol / 4 h / 760 Torr6: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min7: 74 percent / butyl-lithium / hexane; tetrahydrofuran / 2 h / 0 °C8: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 1M aq. NaOH, 30percent aq. hydrogen peroxide / 1.) THF, 4 h, reflux, 2.) 0 deg C, 30 min9: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min, room temperature, 15 min10: 1.) butyl-lithium, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) room temperature, 3 h11: 98 percent / sodium hydroxide / methanol; H2O / 3 h / Ambient temperature12: 95 percent / tetrahydrofuran / 12 h13: 87 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 7 h / -78 °C14: 95 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 2 h / -78 °C15: m-chloroperoxybenzoic acid, 30percent aq. hydrogen peroxide / CDCl3 / 1.) -50 deg C, 15 min, 2.) 0 deg C, 15 min16: 37 percent / toluene / 5 h / 100 °C17: 98 percent / sodium hydroxide / H2O; methanol / 2 h / 0 °C18: 65 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1.) -20 deg C, 1 h, 2.) 0 deg C, 12 h19: 51 percent / aluminium isopropoxide / o-xylene / 8 h / 125 °C21: lithium di-isopropylamide22: tetrabutylammonium fluoride23: hydrogen peroxide, pyridine24: NaBH4 25: pyridine  

Multi-step reaction with 26 steps 1: 69 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / 0 °C2: 1.) dimethyl sulphide, N-chlorosuccinimide, 2.) triethylamine / 1.) toluene, ether, -20 deg C, 2 h, 2.) 30 min3: 63 percent / benzene / 6 h / 80 °C4: 86 percent / ethyl di-isopropylamine / CH2Cl2 / 2 h / Heating5: 70 percent / Dowex 50W X-8 / methanol / 3 h / Ambient temperature6: 95 percent / hydrogen / 10percent Pd-C / methanol / 4 h / 760 Torr7: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min8: 74 percent / butyl-lithium / hexane; tetrahydrofuran / 2 h / 0 °C9: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 1M aq. NaOH, 30percent aq. hydrogen peroxide / 1.) THF, 4 h, reflux, 2.) 0 deg C, 30 min10: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min, room temperature, 15 min11: 1.) butyl-lithium, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) room temperature, 3 h12: 98 percent / sodium hydroxide / methanol; H2O / 3 h / Ambient temperature13: 95 percent / tetrahydrofuran / 12 h14: 87 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 7 h / -78 °C15: 95 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 2 h / -78 °C16: m-chloroperoxybenzoic acid, 30percent aq. hydrogen peroxide / CDCl3 / 1.) -50 deg C, 15 min, 2.) 0 deg C, 15 min17: 37 percent / toluene / 5 h / 100 °C18: 98 percent / sodium hydroxide / H2O; methanol / 2 h / 0 °C19: 65 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1.) -20 deg C, 1 h, 2.) 0 deg C, 12 h20: 51 percent / aluminium isopropoxide / o-xylene / 8 h / 125 °C22: lithium di-isopropylamide23: tetrabutylammonium fluoride24: hydrogen peroxide, pyridine25: NaBH4 26: pyridine  

Multi-step reaction with 24 steps 1: 63 percent / benzene / 6 h / 80 °C2: 86 percent / ethyl di-isopropylamine / CH2Cl2 / 2 h / Heating3: 70 percent / Dowex 50W X-8 / methanol / 3 h / Ambient temperature4: 95 percent / hydrogen / 10percent Pd-C / methanol / 4 h / 760 Torr5: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min6: 74 percent / butyl-lithium / hexane; tetrahydrofuran / 2 h / 0 °C7: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 1M aq. NaOH, 30percent aq. hydrogen peroxide / 1.) THF, 4 h, reflux, 2.) 0 deg C, 30 min8: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min, room temperature, 15 min9: 1.) butyl-lithium, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) room temperature, 3 h10: 98 percent / sodium hydroxide / methanol; H2O / 3 h / Ambient temperature11: 95 percent / tetrahydrofuran / 12 h12: 87 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 7 h / -78 °C13: 95 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 2 h / -78 °C14: m-chloroperoxybenzoic acid, 30percent aq. hydrogen peroxide / CDCl3 / 1.) -50 deg C, 15 min, 2.) 0 deg C, 15 min15: 37 percent / toluene / 5 h / 100 °C16: 98 percent / sodium hydroxide / H2O; methanol / 2 h / 0 °C17: 65 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1.) -20 deg C, 1 h, 2.) 0 deg C, 12 h18: 51 percent / aluminium isopropoxide / o-xylene / 8 h / 125 °C20: lithium di-isopropylamide21: tetrabutylammonium fluoride22: hydrogen peroxide, pyridine23: NaBH4 24: pyridine  

Multi-step reaction with 23 steps 1: 86 percent / ethyl di-isopropylamine / CH2Cl2 / 2 h / Heating2: 70 percent / Dowex 50W X-8 / methanol / 3 h / Ambient temperature3: 95 percent / hydrogen / 10percent Pd-C / methanol / 4 h / 760 Torr4: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min5: 74 percent / butyl-lithium / hexane; tetrahydrofuran / 2 h / 0 °C6: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 1M aq. NaOH, 30percent aq. hydrogen peroxide / 1.) THF, 4 h, reflux, 2.) 0 deg C, 30 min7: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min, room temperature, 15 min8: 1.) butyl-lithium, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) room temperature, 3 h9: 98 percent / sodium hydroxide / methanol; H2O / 3 h / Ambient temperature10: 95 percent / tetrahydrofuran / 12 h11: 87 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 7 h / -78 °C12: 95 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 2 h / -78 °C13: m-chloroperoxybenzoic acid, 30percent aq. hydrogen peroxide / CDCl3 / 1.) -50 deg C, 15 min, 2.) 0 deg C, 15 min14: 37 percent / toluene / 5 h / 100 °C15: 98 percent / sodium hydroxide / H2O; methanol / 2 h / 0 °C16: 65 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1.) -20 deg C, 1 h, 2.) 0 deg C, 12 h17: 51 percent / aluminium isopropoxide / o-xylene / 8 h / 125 °C19: lithium di-isopropylamide20: tetrabutylammonium fluoride21: hydrogen peroxide, pyridine22: NaBH4 23: pyridine  

Multi-step reaction with 21 steps 1: 95 percent / hydrogen / 10percent Pd-C / methanol / 4 h / 760 Torr2: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min3: 74 percent / butyl-lithium / hexane; tetrahydrofuran / 2 h / 0 °C4: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 1M aq. NaOH, 30percent aq. hydrogen peroxide / 1.) THF, 4 h, reflux, 2.) 0 deg C, 30 min5: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min, room temperature, 15 min6: 1.) butyl-lithium, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) room temperature, 3 h7: 98 percent / sodium hydroxide / methanol; H2O / 3 h / Ambient temperature8: 95 percent / tetrahydrofuran / 12 h9: 87 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 7 h / -78 °C10: 95 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 2 h / -78 °C11: m-chloroperoxybenzoic acid, 30percent aq. hydrogen peroxide / CDCl3 / 1.) -50 deg C, 15 min, 2.) 0 deg C, 15 min12: 37 percent / toluene / 5 h / 100 °C13: 98 percent / sodium hydroxide / H2O; methanol / 2 h / 0 °C14: 65 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1.) -20 deg C, 1 h, 2.) 0 deg C, 12 h15: 51 percent / aluminium isopropoxide / o-xylene / 8 h / 125 °C17: lithium di-isopropylamide18: tetrabutylammonium fluoride19: hydrogen peroxide, pyridine20: NaBH4 21: pyridine  

Multi-step reaction with 22 steps 1: 70 percent / Dowex 50W X-8 / methanol / 3 h / Ambient temperature2: 95 percent / hydrogen / 10percent Pd-C / methanol / 4 h / 760 Torr3: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min4: 74 percent / butyl-lithium / hexane; tetrahydrofuran / 2 h / 0 °C5: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 1M aq. NaOH, 30percent aq. hydrogen peroxide / 1.) THF, 4 h, reflux, 2.) 0 deg C, 30 min6: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min, room temperature, 15 min7: 1.) butyl-lithium, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) room temperature, 3 h8: 98 percent / sodium hydroxide / methanol; H2O / 3 h / Ambient temperature9: 95 percent / tetrahydrofuran / 12 h10: 87 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 7 h / -78 °C11: 95 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 2 h / -78 °C12: m-chloroperoxybenzoic acid, 30percent aq. hydrogen peroxide / CDCl3 / 1.) -50 deg C, 15 min, 2.) 0 deg C, 15 min13: 37 percent / toluene / 5 h / 100 °C14: 98 percent / sodium hydroxide / H2O; methanol / 2 h / 0 °C15: 65 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1.) -20 deg C, 1 h, 2.) 0 deg C, 12 h16: 51 percent / aluminium isopropoxide / o-xylene / 8 h / 125 °C18: lithium di-isopropylamide19: tetrabutylammonium fluoride20: hydrogen peroxide, pyridine21: NaBH4 22: pyridine