sodium tetrahydroborate in methanol T=20°C; 4 h;

pyridine; lead(IV) acetate; sodium tetrahydroborate 1) 3.75h, 20 deg C, 2) 3h, 20 deg C; Yield given. Multistep reaction;

1: 98 percent / DMAP; Et3N / CH2Cl2 / 6 h / 20 °C 2: 95 percent / aq. NaIO4 / tetrahydrofuran / 2 h 3: 92 percent / NaBH4 / methanol / 4 h / 20 °C View Scheme

1: 93 percent / aq. HCl / ethanol / 4 h / Heating 2: 98 percent / DMAP; Et3N / CH2Cl2 / 6 h / 20 °C 3: 95 percent / aq. NaIO4 / tetrahydrofuran / 2 h 4: 92 percent / NaBH4 / methanol / 4 h / 20 °C View Scheme

1: 98 percent / DMAP; Et3N / CH2Cl2 / 6 h / 20 °C 2: 95 percent / aq. NaIO4 / tetrahydrofuran / 2 h 3: 92 percent / NaBH4 / methanol / 4 h / 20 °C View Scheme

1: 78 percent / NaH / dimethylformamide / 1) 45 min, 0 deg C, 2) 1.75 h, 20 deg C 2: 71 percent / conc. HCl / H2O; ethanol / 17 h / 100 °C 3: 93 percent / 4-dimethylaminopyridine / CH2Cl2 / 50.5 h / 30 °C 4: 1) lead tetraacetate, pyridine, 2) NaBH4 / 1) 3.75h, 20 deg C, 2) 3h, 20 deg C View Scheme

(i) Ag2O, benzene, (ii) LiAlH4; Multistep reaction;

2: (i) Ag2O, benzene, (ii) LiAlH4 View Scheme

(i) Ag2O, benzene, (ii) LiAlH4; Multistep reaction;