1.1: 19.7 percent / pyridine; CrO3 / 20 h / 20 °C 2.1: Ag2O; 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 20 °C 2.2: NaBH4 / propan-2-ol / 3 h / 20 °C 2.3: 0.32 g / pyridine / 3 h / 90 °C 3.1: 100 percent / KOH / methanol / 20 °C View Scheme

1: 65 percent / chromic anhydride, pyridine 2: pyridine 3: 95 percent / NaBH4 / propan-2-ol 4: 47.7 percent / silver oxide, 4 Angstroem molecular sieves, / 1,2-dichloro-ethane / Ambient temperature 5: NaOMe / methanol View Scheme

1: 65 percent / chromic anhydride, pyridine 2: pyridine 3: 95 percent / NaBH4 / propan-2-ol 4: 47.7 percent / silver oxide, 4 Angstroem molecular sieves, / 1,2-dichloro-ethane / Ambient temperature 5: NaOMe / methanol View Scheme

1: chromic anhydride / pyridine 2: sodium borohydride / propan-2-ol 3: silver oxide / CH2Cl2 4: 0.1M sodium methoxide / methanol View Scheme