1.1: 70 percent / diethyl ether / 1 h / 0 °C 2.1: NaH / tetrahydrofuran / 0 - 20 °C 2.2: 89.4 percent / tetrahydrofuran / 2 h / 20 °C View Scheme

in diethyl ether T=0°C; 3 h;

1: 70 percent / diethyl ether / 3 h / 0 °C 2: 85 percent / NaH / tetrahydrofuran / 0 deg C, then Rt 1 h 3: 1.) Dibal; 2.) silica gel / 1.) petroleum ether, hexane, -60 deg C, then 10 deg C over 1.5 h; 2.) petroleum ether, hexane, water, -30 deg C, then 0 deg C, 1 h 4: NaOH / 2.5 h / Ambient temperature 5: 75 percent / conc. H2SO4 / nitromethane / 0.25 h / 0 °C View Scheme

1.1: 70 percent / diethyl ether / 1 h / 0 °C 2.1: NaH / tetrahydrofuran / 0 - 20 °C 2.2: 89.4 percent / tetrahydrofuran / 2 h / 20 °C 3.1: 86 percent / conc. H2SO4 / nitromethane / 0.5 h / 0 °C 4.1: 95 percent / m-chloroperbenzoic acid / ethyl acetate / 0 - 20 °C 5.1: 96.5 percent / LDA / tetrahydrofuran / -40 - 20 °C 6.1: 66 percent / pyridinium chlorochromate / CH2Cl2 / 0 - 20 °C 7.1: p-toluenesulfonic acid; trimethyl orthoformate 7.2: 89 percent / HCl / acetone 8.1: 72 percent / DIBAL-H / petroleum ether / 1 h / -60 - 20 °C 9.1: nBuLi / tetrahydrofuran / -20 °C 9.2: 79 percent / tetrahydrofuran / 1 h / 0 - 20 °C 10.1: 52 percent / DIBAL-H / petroleum ether / -80 - -20 °C 11.1: 97 percent / HCl / acetone; H2O 12.1: LDA / tetrahydrofuran / 0.17 h / -20 °C 12.2: 69 percent / (+)-(8,8-dichlorocamphorsulfonyl)oxaziridine / tetrahydrofuran / 1.25 h / -20 - 20 °C 13.1: HBr / CH2Cl2 / 0 °C 14.1: 1,2-epoxybutane / ethyl acetate / 24 h / 20 °C 15.1: 55 percent / various solvent(s) / 20 h / 63 °C View Scheme

1.1: 70 percent / diethyl ether / 1 h / 0 °C 2.1: NaH / tetrahydrofuran / 0 - 20 °C 2.2: 89.4 percent / tetrahydrofuran / 2 h / 20 °C 3.1: conc. H2SO4 / nitromethane / 0.5 h / 0 °C View Scheme

1: 70 percent / diethyl ether / 3 h / 0 °C 2: 85 percent / NaH / tetrahydrofuran / 0 deg C, then Rt 1 h View Scheme

lithium aluminium tetrahydride in tetrahydrofuran; diethyl ether

1: 70 percent / diethyl ether / 3 h / 0 °C 2: 85 percent / NaH / tetrahydrofuran / 0 deg C, then Rt 1 h 3: 1.) Dibal; 2.) silica gel / 1.) petroleum ether, hexane, -60 deg C, then 10 deg C over 1.5 h; 2.) petroleum ether, hexane, water, -30 deg C, then 0 deg C, 1 h View Scheme

1: 1.) KOH 2.) LiAlH4 3: NaI 4: 86 percent / NaOEt / ethanol / Heating View Scheme

potassium hydroxide in water; ethylene glycol 7.5 h; Heating;