1: DIBAL / toluene / 1 h / -78 °C 2: KOtBu / dimethylformamide / Ambient temperature 3: 79 percent / CrO3 / acetone / 1) 0 deg C, 30 min, 2)r.t., 1.5 h 4: SOCl2 / 2 h / Heating View Scheme

2: Na(Hg), MeOH / tetrahydrofuran / 8 h / -20 °C 3: aq. KOH / ethanol / 1 h / Heating 4: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min View Scheme

1: pyridinium chlorochromate (PCC), sodium acetate / CH2Cl2 / 1.5 h / Ambient temperature 3: Na(Hg), MeOH / tetrahydrofuran / 8 h / -20 °C 4: aq. KOH / ethanol / 1 h / Heating 5: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min View Scheme

1: aq. KOH / ethanol / 1 h / Heating 2: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min View Scheme

thionyl chloride 1.) RT, 18 h, 2.) 100 deg C, 30 min;

1: Et3N / CH2Cl2 / 1.) 0 deg C, 30 min, 2.) RT, 1 h 2: 1.) NaH, 2.) KI / 1.) DMF, THF, RT, 15 min, 2.) DMF, THF, 80 deg C, 3.5 h 3: 86 percent / DMSO, NaCl / H2O / 3 h / 170 °C 4: 96 percent / LiAlH4 / diethyl ether / 15 h / Ambient temperature 5: Et3N / CH2Cl2 / 1.) 0 deg C, 30 min, 2.) RT, 1 h 6: dimethylsulfoxide / 3 h / 140 °C 7: 89 percent / aq. NaOH / methanol / 15 h / Heating 8: SOCl2 / 2 h / Heating View Scheme

1: 1.) NaH, 2.) KI / 1.) DMF, THF, RT, 15 min, 2.) DMF, THF, 80 deg C, 3.5 h 2: 86 percent / DMSO, NaCl / H2O / 3 h / 170 °C 3: 96 percent / LiAlH4 / diethyl ether / 15 h / Ambient temperature 4: Et3N / CH2Cl2 / 1.) 0 deg C, 30 min, 2.) RT, 1 h 5: dimethylsulfoxide / 3 h / 140 °C 6: 89 percent / aq. NaOH / methanol / 15 h / Heating 7: SOCl2 / 2 h / Heating View Scheme

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

1: 89 percent / aq. NaOH / methanol / 15 h / Heating 2: SOCl2 / 2 h / Heating View Scheme