sulfuric acid in methanol T=20°C; 3.5 h;

1: 51 percent / HCl; NaBH3CN / methanol / 24 h / 20 °C 2: 83 percent / H2SO4 / methanol / 3.5 h / 20 °C View Scheme

1: 83 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 2 h / -78 - -20 °C 2: 51 percent / HCl; NaBH3CN / methanol / 24 h / 20 °C 3: 83 percent / H2SO4 / methanol / 3.5 h / 20 °C View Scheme

1: 95 percent / imidazole / dimethylformamide / 0.5 h / 0 °C 2: 99 percent / LiAlH4 / diethyl ether / 1.75 h / 20 °C 3: 3.59 g / pyridinium chlorochromate / CH2Cl2 / 5 h / 0 °C 4: 1.99 g / diethyl ether / 1 h / -78 °C 5: 83 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 2 h / -78 - -20 °C 6: 51 percent / HCl; NaBH3CN / methanol / 24 h / 20 °C 7: 83 percent / H2SO4 / methanol / 3.5 h / 20 °C View Scheme

1: 3.59 g / pyridinium chlorochromate / CH2Cl2 / 5 h / 0 °C 2: 1.99 g / diethyl ether / 1 h / -78 °C 3: 83 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 2 h / -78 - -20 °C 4: 51 percent / HCl; NaBH3CN / methanol / 24 h / 20 °C 5: 83 percent / H2SO4 / methanol / 3.5 h / 20 °C View Scheme

1: 99 percent / LiAlH4 / diethyl ether / 1.75 h / 20 °C 2: 3.59 g / pyridinium chlorochromate / CH2Cl2 / 5 h / 0 °C 3: 1.99 g / diethyl ether / 1 h / -78 °C 4: 83 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 2 h / -78 - -20 °C 5: 51 percent / HCl; NaBH3CN / methanol / 24 h / 20 °C 6: 83 percent / H2SO4 / methanol / 3.5 h / 20 °C View Scheme

1: 1.99 g / diethyl ether / 1 h / -78 °C 2: 83 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 2 h / -78 - -20 °C 3: 51 percent / HCl; NaBH3CN / methanol / 24 h / 20 °C 4: 83 percent / H2SO4 / methanol / 3.5 h / 20 °C View Scheme