sodium tetrahydroborate in ethanol 2 h;

isopropyl alcohol

1: With oxalyl dichloride; dimethyl sulfoxide in dichloromethane T=-78°C; 0.5 h; 2: With triethylamine in dichloromethane T=18 - 25°C; 1 h;

1: 7.5 g / m-chloroperoxybenzoic acid / CHCl3 / 1) 0 deg C, 1h, 2) room temp., 30 min 2: 5.0 g / Jones reagent / acetone 3: tin tetrachloride / diethyl ether / 4 h 4: 45 percent / 10percent sulfuric acid / H2O; methanol / 16 h / Heating View Scheme

1: 7.5 g / m-chloroperoxybenzoic acid / CHCl3 / 1) 0 deg C, 1h, 2) room temp., 30 min 2: 5.0 g / Jones reagent / acetone View Scheme