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: 92 percent / aq. NaOH / methanol / 15 h / Heating 4: SOCl2 / 2 h / Heating 5: diethyl ether / 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: 92 percent / aq. NaOH / methanol / 15 h / Heating 4: 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: 1.) NaH, 2.) KI / 1.) DMF, THF, RT, 15 min, 2.) DMF, THF, 80 deg C, 3.5 h 6: 89 percent / DMSO, NaCl / H2O / 3 h / 170 °C 7: 94 percent / LiAlH4 / diethyl ether / 15 h / Ambient temperature 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