1: NaOH; H2O / methanol / 12 h / 80 °C 2: 99 percent / LiAlH4 / diethyl ether 3: 97 percent / Et3N; 4-pyrrolidinopyridine / 0.33 h / 20 °C 4: 63.5 percent / AlCl3 / CS2 / 1.5 h / 0 - 5 °C 5: 68 percent / p-TsOH*H2O / benzene / 24 h / Heating 6: 99 percent / NaOH; MeOH / 0.5 h / 20 °C 7: 89 percent / Jones reagent / acetone / 0 °C 8: 92 percent / diethyl ether / 0 °C 9: 89 percent / HCl; H2O / tetrahydrofuran / 15 h / 20 °C 10: 95 percent / NaBH4 / methanol; tetrahydrofuran / 0.5 h / 0 °C 11: 44 percent / K2CO3; KI / dimethylformamide; toluene / 7 h / Heating View Scheme

1: NaOH; H2O / methanol / 12 h / 80 °C 2: 99 percent / LiAlH4 / diethyl ether 3: 97 percent / Et3N; 4-pyrrolidinopyridine / 0.33 h / 20 °C 4: 63.5 percent / AlCl3 / CS2 / 1.5 h / 0 - 5 °C View Scheme

1: NaOH; H2O / methanol / 12 h / 80 °C 2: 99 percent / LiAlH4 / diethyl ether 3: 97 percent / Et3N; 4-pyrrolidinopyridine / 0.33 h / 20 °C View Scheme

sodium tetrahydroborate in tetrahydrofuran T=20°C;

sodium chloride; sodium hydrogencarbonate in tetrahydrofuran; water

sodium

1: methanephosphonic acid dimethyl ester With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.5 h; 2: 2-Methyl-2-phenylpropionate, methyl ester in tetrahydrofuran; hexane T=-78°C; 2.16667 h;

n-butyllithium in tetrahydrofuran; hexane; water; ethyl acetate

1: LiAlH4 / diethyl ether / 0 °C 2: PCC / CH2Cl2 View Scheme