0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; triethylamine; pyridinium chlorochromate 1.) CH2Cl2, 2.) CH2Cl2; Multistep reaction;

1: 77 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / CH2Cl2 / 2 h / Ambient temperature 3: 84 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / CH2Cl2 / 2 h / Ambient temperature 4: 1.) sodium hydride / 1.) DMF, 80 deg C, 2.5 h, 2.) DMF, 80 deg C, 24 h View Scheme

1: HBr 2: KBr, TEMPO, NaOCl, NaHCO3 / CH2Cl2; H2O / 0.05 h / pH 9; below 10 deg C 3: HCl gas / CH2Cl2; methanol / 0.5 h / 20 °C View Scheme

1: NaH; Bu4NI / tetrahydrofuran 2: (COCl)2; DMSO / CH2Cl2 / -78 - 0 °C View Scheme

1: pyridine / CH2Cl2 / Ambient temperature 2: NaI / acetone / 2 h / Heating 3: PPTS / CH2Cl2 / Ambient temperature 4: 1) bipyridyl, n-BuLi / 1) THF, hexane, -78 deg C, 1h, 2) HMPA, RT, 24h 5: 1) disiamylborane, 2) HOAc / 1) THF, 0 deg C, 1h, 2) RT, 4h 6: 71 percent / 3N HCl / methanol / 1.5 h / Ambient temperature 7: 88 percent / pyridine / acetonitrile / 1 h / 0 °C 8: 43 percent / t-BuOOH, D-(-)-DIPT, Ti(O-i-Pr)4, molecular sieves 4 Angstroem / CH2Cl2 / 16 h / -21 °C 9: t-BuOOH, Ti(O-i-Pr)4, L-(+)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / -21 °C 10: PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1 h / 0 °C 11: 1N NaOH / methanol / 1 h / 0 °C 12: 1) Bu3SnLi, 2) I2 / 1) THF, 0 deg C, 3h, 2) Et2O, 0 deg C 13: imidazole / dimethylformamide / Ambient temperature 14: 1) disiamylborane, 2) LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h, 2) 40 degC, 12h 15: 79 percent / n-Bu4NF / tetrahydrofuran / 18 h / Ambient temperature View Scheme

1: sodium / 70 °C / zuletzt bei 140grad 2: Cr2O3-H2SO4 View Scheme

DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) in benzene T=20 - 25°C; 2 h; Further byproducts given;

1: 45 percent / triethylamine / CH2Cl2 / 1.17 h / 0 - 20 °C 2: triethylamine / CH2Cl2 / 0.5 h / 0 °C 3: 54 percent / NaI / acetone / 2 h / Heating 4: 97 percent / NaH / dimethylformamide / 1 h / Heating 5: 289 mg / KOH / ethanol; H2O / 2 h / 20 °C 6: NaH / dimethylformamide / 1 h / 20 °C View Scheme

1: 45 percent / triethylamine / CH2Cl2 / 1.17 h / 0 - 20 °C 2: triethylamine / CH2Cl2 / 0.5 h / 0 °C 3: 54 percent / NaI / acetone / 2 h / Heating 4: 97 percent / NaH / dimethylformamide / 1 h / Heating 5: 289 mg / KOH / ethanol; H2O / 2 h / 20 °C 6: diisopropylethylamine / CH2Cl2 / 1.5 h / 20 °C View Scheme

1: 45 percent / triethylamine / CH2Cl2 / 1.17 h / 0 - 20 °C 2: triethylamine / CH2Cl2 / 0.5 h / 0 °C View Scheme