dipyridinium dichromate in dichloromethane T=20°C; 2 h; Molecular sieve;

1: 1) Mg / 2) Li2CuCl4 / 1) THF, 2) THF a) 1 h, b) -10 deg C, 3 h 2: 81.2 percent / pTsOH / methanol / 6 h / Ambient temperature 3: 62 percent / PCC / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 71.8 percent / PBr3, pyridine / diethyl ether / 1) overnight, 2) reflux, 0.5 h 2: 1) Mg / 2) Li2CuCl4 / 1) THF, 2) THF a) 1 h, b) -10 deg C, 3 h 3: 81.2 percent / pTsOH / methanol / 6 h / Ambient temperature 4: 62 percent / PCC / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 1) 50percent NaH / 1) THF, room temp.; 2) THF, 2 h 2: 92.3 percent / LiAlH4 / ethanol; diethyl ether / 0.5 h / 0 - 5 °C 3: 71.8 percent / PBr3, pyridine / diethyl ether / 1) overnight, 2) reflux, 0.5 h 4: 1) Mg / 2) Li2CuCl4 / 1) THF, 2) THF a) 1 h, b) -10 deg C, 3 h 5: 81.2 percent / pTsOH / methanol / 6 h / Ambient temperature 6: 62 percent / PCC / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 75.8 percent / PCC / CH2Cl2 / 1 h / Ambient temperature 2: 1) 50percent NaH / 1) THF, room temp.; 2) THF, 2 h 3: 92.3 percent / LiAlH4 / ethanol; diethyl ether / 0.5 h / 0 - 5 °C 4: 71.8 percent / PBr3, pyridine / diethyl ether / 1) overnight, 2) reflux, 0.5 h 5: 1) Mg / 2) Li2CuCl4 / 1) THF, 2) THF a) 1 h, b) -10 deg C, 3 h 6: 81.2 percent / pTsOH / methanol / 6 h / Ambient temperature 7: 62 percent / PCC / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 92.3 percent / LiAlH4 / ethanol; diethyl ether / 0.5 h / 0 - 5 °C 2: 71.8 percent / PBr3, pyridine / diethyl ether / 1) overnight, 2) reflux, 0.5 h 3: 1) Mg / 2) Li2CuCl4 / 1) THF, 2) THF a) 1 h, b) -10 deg C, 3 h 4: 81.2 percent / pTsOH / methanol / 6 h / Ambient temperature 5: 62 percent / PCC / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 78 percent / PTSA / methanol / 6 h / Ambient temperature 2: 80 percent / pyridinium fluorochromate / CH2Cl2 / 0.5 h View Scheme

1: 1.) lithium amide / 1.) ammonia, 2 h, 2.) THF, -33 deg C, 6 h 2: 62 percent / triphenyl phosphinem, carbon tetrachloride / 7 h / Heating 3: 1.) CuI / 1.) ether, room temperature, 1 h, 2.) room temperature, 5 h 4: 0.280 g / sodium, liq. ammonia / 0.5 h 5: 78 percent / PTSA / methanol / 6 h / Ambient temperature 6: 80 percent / pyridinium fluorochromate / CH2Cl2 / 0.5 h View Scheme

1: 1.) lithium amide / 1.) ammonia, 2 h, 2.) THF, -33 deg C, 6 h 2: 62 percent / triphenyl phosphinem, carbon tetrachloride / 7 h / Heating 3: 1.) CuI / 1.) ether, room temperature, 1 h, 2.) room temperature, 5 h 4: 0.280 g / sodium, liq. ammonia / 0.5 h 5: 78 percent / PTSA / methanol / 6 h / Ambient temperature 6: 80 percent / pyridinium fluorochromate / CH2Cl2 / 0.5 h View Scheme

1: 62 percent / triphenyl phosphinem, carbon tetrachloride / 7 h / Heating 2: 1.) CuI / 1.) ether, room temperature, 1 h, 2.) room temperature, 5 h 3: 0.280 g / sodium, liq. ammonia / 0.5 h 4: 78 percent / PTSA / methanol / 6 h / Ambient temperature 5: 80 percent / pyridinium fluorochromate / CH2Cl2 / 0.5 h View Scheme