1: 89 percent / NH3, MeONa / methanol / 8 h 2: 73 percent / LiAlH4 / tetrahydrofuran; diethyl ether / Heating 3: 75 percent / Et3N / toluene / 6 h / Heating 4: 52 percent / 2 N HCl / 5 h / Heating 5: 1.) LiAlH4, 2.) aq. NaOH / 1.) Et2O, reflux, 3 h, 2.) Et2O, RT, 30 min View Scheme

1: 87 percent / Et3N / 12 h / 100 °C 2: 89 percent / NH3, MeONa / methanol / 8 h 3: 73 percent / LiAlH4 / tetrahydrofuran; diethyl ether / Heating 4: 75 percent / Et3N / toluene / 6 h / Heating 5: 52 percent / 2 N HCl / 5 h / Heating 6: 1.) LiAlH4, 2.) aq. NaOH / 1.) Et2O, reflux, 3 h, 2.) Et2O, RT, 30 min View Scheme

1: 75 percent / Et3N / toluene / 6 h / Heating 2: 52 percent / 2 N HCl / 5 h / Heating 3: 1.) LiAlH4, 2.) aq. NaOH / 1.) Et2O, reflux, 3 h, 2.) Et2O, RT, 30 min View Scheme

1: 73 percent / LiAlH4 / tetrahydrofuran; diethyl ether / Heating 2: 75 percent / Et3N / toluene / 6 h / Heating 3: 52 percent / 2 N HCl / 5 h / Heating 4: 1.) LiAlH4, 2.) aq. NaOH / 1.) Et2O, reflux, 3 h, 2.) Et2O, RT, 30 min View Scheme

sodium hydroxide; lithium aluminium tetrahydride 1.) Et2O, reflux, 3 h, 2.) Et2O, RT, 30 min; Yield givenMultistep reaction;

1: 52 percent / 2 N HCl / 5 h / Heating 2: 1.) LiAlH4, 2.) aq. NaOH / 1.) Et2O, reflux, 3 h, 2.) Et2O, RT, 30 min View Scheme