sulfuric acid in dichloromethane

3 A molecular sieve; trifluoroacetic acid in dichloromethane 0.333333 h; Ambient temperature;

3: 99 percent / DMSO, (COCl)2, Et3N / CH2Cl2 4: 96 percent / PPh3 / benzene / 80 °C 5: 84 percent / n-BuLi / tetrahydrofuran / -78 °C 6: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) oxidation 7: 1.) camphorsulfonic acid, 2.) n-Bu4NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C 8: 88 percent / H2 / Lindlar / methanol 9: 1.) DMSO,(COCl)2, Et3N, 2.) CSA / 1.) CH2Cl2, 2.) CH2Cl2, room temperature 10: (C6H11)2NMgBr / methanol / -55 °C 11: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86) View Scheme

1: NaH / dimethylformamide; tetrahydrofuran / 0 °C 2: H2 / Pd-C / ethyl acetate / Ambient temperature 3: tetrahydrofuran / -78 °C 4: 1.) O3, 2.) NaBH4 / 1.) CH2Cl2, -78 deg C 5: Et3N / 0 °C 6: 1N-HCl / tetrahydrofuran / Ambient temperature 7: K2CO3 / methanol 8: NaH / tetrahydrofuran / Ambient temperature 9: camphorsulfonic acid / CH2Cl2 / 0 °C 10: DMSO, (COCl)2, Et3N / CH2Cl2 11: 28 percent / (Ph3P)3RhCl / acetonitrile / 160 °C 12: DDQ / CH2Cl2; H2O 13: DMSO, (COCl)2 / CH2Cl2 14: TsOH / benzene 15: H2 / Pd-C / ethyl acetate 16: CrO3, H2SO4 / acetone 17: 2N-HCl / tetrahydrofuran / Ambient temperature 18: (C6H11)2NMgBr / methanol / -55 °C 19: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86) View Scheme

1: camphorsulfonic acid / Ambient temperature 2: H2 / Pd-C / ethanol / Ambient temperature 3: DMSO, (COCl)2, Et3N 4: NaH / dimethylformamide; tetrahydrofuran / 0 °C 5: H2 / Pd-C / ethyl acetate / Ambient temperature 6: tetrahydrofuran / -78 °C 7: 1.) O3, 2.) NaBH4 / 1.) CH2Cl2, -78 deg C 8: Et3N / 0 °C 9: 1N-HCl / tetrahydrofuran / Ambient temperature 10: K2CO3 / methanol 11: NaH / tetrahydrofuran / Ambient temperature 12: camphorsulfonic acid / CH2Cl2 / 0 °C 13: DMSO, (COCl)2, Et3N / CH2Cl2 14: 28 percent / (Ph3P)3RhCl / acetonitrile / 160 °C 15: DDQ / CH2Cl2; H2O 16: DMSO, (COCl)2 / CH2Cl2 17: TsOH / benzene 18: H2 / Pd-C / ethyl acetate 19: CrO3, H2SO4 / acetone 20: 2N-HCl / tetrahydrofuran / Ambient temperature 21: (C6H11)2NMgBr / methanol / -55 °C 22: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86) View Scheme

1: H2 / Pd-C / ethanol / Ambient temperature 2: DMSO, (COCl)2, Et3N 3: NaH / dimethylformamide; tetrahydrofuran / 0 °C 4: H2 / Pd-C / ethyl acetate / Ambient temperature 5: tetrahydrofuran / -78 °C 6: 1.) O3, 2.) NaBH4 / 1.) CH2Cl2, -78 deg C 7: Et3N / 0 °C 8: 1N-HCl / tetrahydrofuran / Ambient temperature 9: K2CO3 / methanol 10: NaH / tetrahydrofuran / Ambient temperature 11: camphorsulfonic acid / CH2Cl2 / 0 °C 12: DMSO, (COCl)2, Et3N / CH2Cl2 13: 28 percent / (Ph3P)3RhCl / acetonitrile / 160 °C 14: DDQ / CH2Cl2; H2O 15: DMSO, (COCl)2 / CH2Cl2 16: TsOH / benzene 17: H2 / Pd-C / ethyl acetate 18: CrO3, H2SO4 / acetone 19: 2N-HCl / tetrahydrofuran / Ambient temperature 20: (C6H11)2NMgBr / methanol / -55 °C 21: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86) View Scheme

1: DMSO, (COCl)2 / CH2Cl2 2: TsOH / benzene 3: H2 / Pd-C / ethyl acetate 4: CrO3, H2SO4 / acetone 5: 2N-HCl / tetrahydrofuran / Ambient temperature 6: (C6H11)2NMgBr / methanol / -55 °C 7: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86) View Scheme

1: TsOH / benzene 2: H2 / Pd-C / ethyl acetate 3: CrO3, H2SO4 / acetone 4: 2N-HCl / tetrahydrofuran / Ambient temperature 5: (C6H11)2NMgBr / methanol / -55 °C 6: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86) View Scheme

1: H2 / Pd-C / ethyl acetate 2: CrO3, H2SO4 / acetone 3: 2N-HCl / tetrahydrofuran / Ambient temperature 4: (C6H11)2NMgBr / methanol / -55 °C 5: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86) View Scheme

1: CrO3, H2SO4 / acetone 2: H2 / Pd-C / ethyl acetate 3: PCC, molecular sieves / CH2Cl2 4: (C6H11)2NMgBr / methanol / -55 °C 5: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86) View Scheme