1: With sodium ethanolate in diethyl ether T=0 - 20°C; Inert atmosphere; 2: With sulfuric acid in water 18 h; Reflux;

1: With oxalyl dichloride; dimethyl sulfoxide in dichloromethane T=-78°C; 0.5 h; 2: With triethylamine in dichloromethane T=18 - 25°C; 1 h;

sulfuric acid in water Inert atmosphereReflux;

1: sodium / toluene; methanol / 20 - 105 °C / Inert atmosphere 2: sulfuric acid / water / Inert atmosphere; Reflux View Scheme

sodium tetrahydroborate in ethanol 2 h;

isopropyl alcohol

1.1: dichloromethane / 0.08 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: water; lithium chloride / dimethyl sulfoxide / 5 h / 185 °C / Inert atmosphere View Scheme

1.1: dichloromethane / 0.08 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: sodium tetrahydroborate; water / tetrahydrofuran / 2.5 h / 0 - 20 °C / Inert atmosphere 3.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C 6.1: diisobutylaluminium hydride / tetrahydrofuran; n-heptane / 4.5 h / -78 - 0 °C / Inert atmosphere 7.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere 8.1: lithium triethylborohydride / tetrahydrofuran / -30 - 20 °C / Inert atmosphere 9.1: palladium 10 on activated carbon; hydrogen / methanol / 1500.15 Torr 10.1: dibromo-difluoro-methane; tert-butyl alcohol / dichloromethane / 1.5 h / 60 °C / Inert atmosphere; Microwave irradiation View Scheme

1: 6.8 g / sodium borohydride / ethanol / 0.5 h 2: 7.5 g / m-chloroperoxybenzoic acid / CHCl3 / 1) 0 deg C, 1h, 2) room temp., 30 min 3: 5.0 g / Jones reagent / acetone 4: tin tetrachloride / diethyl ether / 4 h 5: 45 percent / 10percent sulfuric acid / H2O; methanol / 16 h / Heating View Scheme

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