1: 1.) SOCl2, 2.) NH3 (gas) / 1.) reflux, 3 h, 2.) THF, RT, 3 h 2: LiAlH4 / diethyl ether / a) RT, 10.5 h, b) reflux, 4 h 3: 1.) SOCl2, HMPA, 2.) Et3N / 1.) -5 deg C, 10 min, 2.) Et2O, RT, overnight 4: 37.2 percent / CrO3 / acetic acid; H2O / Ambient temperature 5: 68 percent / HBr / acetic acid / 1.5 h / Ambient temperature View Scheme

1: LiAlH4 / diethyl ether / a) RT, 10.5 h, b) reflux, 4 h 2: 1.) SOCl2, HMPA, 2.) Et3N / 1.) -5 deg C, 10 min, 2.) Et2O, RT, overnight 3: 37.2 percent / CrO3 / acetic acid; H2O / Ambient temperature 4: 68 percent / HBr / acetic acid / 1.5 h / Ambient temperature View Scheme

1: 98.5 percent / 86percent KOH / ethanol / 2 h / Heating 2: 1.) SOCl2, 2.) NH3 (gas) / 1.) reflux, 3 h, 2.) THF, RT, 3 h 3: LiAlH4 / diethyl ether / a) RT, 10.5 h, b) reflux, 4 h 4: 1.) SOCl2, HMPA, 2.) Et3N / 1.) -5 deg C, 10 min, 2.) Et2O, RT, overnight 5: 37.2 percent / CrO3 / acetic acid; H2O / Ambient temperature 6: 68 percent / HBr / acetic acid / 1.5 h / Ambient temperature View Scheme

1: 37.2 percent / CrO3 / acetic acid; H2O / Ambient temperature 2: 68 percent / HBr / acetic acid / 1.5 h / Ambient temperature View Scheme

1: 90 percent / Jones reagent / acetone 2: 90 percent / NH2NH2*H2O / ethanol / Heating View Scheme

1: 98.5 percent / Jones reagent / acetone 2: 68 percent / HBr / acetic acid / 1.5 h / Ambient temperature View Scheme

1: 1.) SOCl2, HMPA, 2.) Et3N / 1.) -5 deg C, 10 min, 2.) Et2O, RT, overnight 2: 37.2 percent / CrO3 / acetic acid; H2O / Ambient temperature 3: 68 percent / HBr / acetic acid / 1.5 h / Ambient temperature View Scheme