in diethyl ether; benzene T=-78°C; 0.5 h;

1: 67 percent / NaBH4, NaHCO3 / H2O / 1 h / Ambient temperature 2: 83 percent / diethyl ether; benzene / 0.5 h / -78 °C View Scheme

1: 72 percent / Zn / acetic acid / 24 h / 50 °C 2: 67 percent / NaBH4, NaHCO3 / H2O / 1 h / Ambient temperature 3: 83 percent / diethyl ether; benzene / 0.5 h / -78 °C View Scheme

1: SOCl2 2: 4.2 g / tetrahydrofuran; diethyl ether / 0.5 h 3: 72 percent / Zn / acetic acid / 24 h / 50 °C 4: 67 percent / NaBH4, NaHCO3 / H2O / 1 h / Ambient temperature 5: 83 percent / diethyl ether; benzene / 0.5 h / -78 °C View Scheme

1: 4.2 g / tetrahydrofuran; diethyl ether / 0.5 h 2: 72 percent / Zn / acetic acid / 24 h / 50 °C 3: 67 percent / NaBH4, NaHCO3 / H2O / 1 h / Ambient temperature 4: 83 percent / diethyl ether; benzene / 0.5 h / -78 °C View Scheme