1: n-Bu4NBH4 / methanol / -78 °C 2: 88 percent / triflic anhydride; 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.08 h / 0 °C 3: HCl / tetrahydrofuran; H2O / 2 h / 25 °C 4: Jones reagent / acetone / 6 h / 0 - 25 °C 5: 42 mg / HCl / H2O / 48 h / 100 °C View Scheme

1: n-Bu4NBH4 / methanol / -78 °C 2: 88 percent / NaH / dimethylformamide / 6 h / 0 °C 3: 80 percent / HCl / tetrahydrofuran; H2O / 2 h / 25 °C 4: Jones reagent / acetone / 5 h / 0 - 25 °C 5: 60 mg / HCl / H2O / 48 h / 100 °C View Scheme