tetrabutyl ammonium fluoride in tetrahydrofuran 2 h;

sodium tetrahydroborate in methanol 0.166667 h;

1: 91 percent / NaBH4 / methanol / 0.17 h 2: 80 percent / hydrogen, aq. conc. HCl / PtO2 / ethanol / 24 h / 2280 Torr 3: 97 percent / KHCO3 / methanol / 96 h 4: 64 percent / NaH, 4 Angstroem molecular sieves / dimethylformamide / 1.5 h / 20 °C 5: O3 / CH2Cl2; methanol / 1 h 6: methanol / 0.67 h / Heating 7: <<(C6H5)3P>Cu>BH4 / CHCl3 / 4 h / Heating View Scheme

1: 91 percent / NaBH4 / methanol / 0.17 h 2: 80 percent / hydrogen, aq. conc. HCl / PtO2 / ethanol / 24 h / 2280 Torr 3: 97 percent / KHCO3 / methanol / 96 h 4: 64 percent / NaH, 4 Angstroem molecular sieves / dimethylformamide / 1.5 h / 20 °C 5: O3 / CH2Cl2; methanol / 1 h View Scheme