hydrogen; palladium on activated charcoal in ethanol T=40°C; P=1034.3 Torr; 12 h;

1: Et3N / toluene / 3 h / Heating 2: NaH / dimethylformamide 3: B(OH)3, (EtO)3B / Heating 4: 1.) Et3N, 2.) Et3N, water / 1.) diethyl ether, RT, 5 h, 2.) diethyl ether, reflux, 2 h 5: CHCl3; propan-2-ol; dimethylformamide / 12 h / 50 °C 6: H2 / 10percent Pd/C / ethanol / 12 h / 40 °C / 1034.3 Torr View Scheme

1: NaH / dimethylformamide 2: B(OH)3, (EtO)3B / Heating 3: 1.) Et3N, 2.) Et3N, water / 1.) diethyl ether, RT, 5 h, 2.) diethyl ether, reflux, 2 h 4: CHCl3; propan-2-ol; dimethylformamide / 12 h / 50 °C 5: H2 / 10percent Pd/C / ethanol / 12 h / 40 °C / 1034.3 Torr View Scheme

1: 1.) Et3N, 2.) Et3N, water / 1.) diethyl ether, RT, 5 h, 2.) diethyl ether, reflux, 2 h 2: CHCl3; propan-2-ol; dimethylformamide / 12 h / 50 °C 3: H2 / 10percent Pd/C / ethanol / 12 h / 40 °C / 1034.3 Torr View Scheme

1: CHCl3; propan-2-ol; dimethylformamide / 12 h / 50 °C 2: H2 / 10percent Pd/C / ethanol / 12 h / 40 °C / 1034.3 Torr View Scheme

1: B(OH)3, (EtO)3B / Heating 2: 1.) Et3N, 2.) Et3N, water / 1.) diethyl ether, RT, 5 h, 2.) diethyl ether, reflux, 2 h 3: CHCl3; propan-2-ol; dimethylformamide / 12 h / 50 °C 4: H2 / 10percent Pd/C / ethanol / 12 h / 40 °C / 1034.3 Torr View Scheme