sodium hydroxide; sodium tetrahydroborate; mercury(II) diacetate; dihydrogen peroxide 1) THF, 16 h, room temperature; 2) THF, 70 deg C, 1 h; Yield given. Multistep reaction;

1: 1.) NaBH4, Hg(OAc)2, 2.) aq. H2O2, aq. NaOH / 1) THF, 16 h, room temperature; 2) THF, 70 deg C, 1 h 2: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h View Scheme

1.1: 100 percent / CH2Cl2 / 0.17 h / 0 °C 2.1: 72 percent / t-BuOK; 18-crown-6 / petroleum ether / 2 h / Heating 3.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 3.2: tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.25 h / -78 °C 4.1: 97 percent / PtO2 / ethyl acetate / 12 h / 20 °C 5.1: 80 percent / HCl; H2O / methanol / 12 h / 60 °C 6.1: 71 percent / DCC / CH2Cl2 / 12 h 7.1: NH3; H2O / CHCl3; methanol / 12 h / 20 °C 8.1: H2O2; H2O / 12 h / 20 °C View Scheme