1: 92 percent / aq. NaOH / methanol / 15 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 2 h / Heating View Scheme

novozyme 435 T=25°C; 45 h;

1: 92 percent / aq. NaOH / methanol / 15 h / Heating 2: SOCl2 / 2 h / Heating View Scheme

1: 96 percent / LiAlH4 / diethyl ether / 15 h / Ambient temperature 2: Et3N / CH2Cl2 / 1.) 0 deg C, 30 min, 2.) RT, 1 h 3: 1.) NaH, 2.) KI / 1.) DMF, THF, RT, 15 min, 2.) DMF, THF, 80 deg C, 3.5 h 4: 89 percent / DMSO, NaCl / H2O / 3 h / 170 °C 5: 94 percent / LiAlH4 / diethyl ether / 15 h / Ambient temperature View Scheme

1: aq. KOH / ethanol / 1 h / Heating 2: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 3: diethyl ether / 72 h / Ambient temperature 4: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme

1: 96 percent / LiAlH4 / diethyl ether / 15 h / Ambient temperature 2: Et3N / CH2Cl2 / 1.) 0 deg C, 30 min, 2.) RT, 1 h 3: dimethylsulfoxide / 3 h / 140 °C 4: 89 percent / aq. NaOH / methanol / 15 h / Heating 5: SOCl2 / 2 h / Heating View Scheme