sodium hydrogencarbonate in N,N-dimethyl-formamide T=20°C; 40 h;

diazomethane in diethyl ether

formaldehyd; boron trifluoride diethyl etherate in water; acetone 120 h; Ambient temperature;

1: 8 percent / 30percent H2O2, Potassium carbonate / methanol; acetonitrile; H2O / 5 h / 0 °C 2: 82 percent / NaBH4, NaOMe / methanol / 0.5 h 3: 11 percent / paraformaldehyde, BF3*Et2O / acetone; H2O / 120 h / Ambient temperature View Scheme

1: 96 percent / sodium bicarbonate / CH2Cl2 / 72 h / 30 °C 2: 92 percent / zinc powder / tetrahydrofuran / 3 h / Heating 3: 8 percent / 30percent H2O2, Potassium carbonate / methanol; acetonitrile; H2O / 5 h / 0 °C 4: 82 percent / NaBH4, NaOMe / methanol / 0.5 h 5: 11 percent / paraformaldehyde, BF3*Et2O / acetone; H2O / 120 h / Ambient temperature View Scheme

1: 92 percent / zinc powder / tetrahydrofuran / 3 h / Heating 2: 8 percent / 30percent H2O2, Potassium carbonate / methanol; acetonitrile; H2O / 5 h / 0 °C 3: 82 percent / NaBH4, NaOMe / methanol / 0.5 h 4: 11 percent / paraformaldehyde, BF3*Et2O / acetone; H2O / 120 h / Ambient temperature View Scheme

1: 82 percent / NaBH4, NaOMe / methanol / 0.5 h 2: 11 percent / paraformaldehyde, BF3*Et2O / acetone; H2O / 120 h / Ambient temperature View Scheme

in diethyl ether

1: imidazole / dimethylformamide / 2 h / Ambient temperature 2: 95 percent / 30percent hydrogen peroxide, 3 M aq. lithium hydroxide / methanol / 5 h / -30 - -25 °C 3: aq. sodium hydrogen carbonate, aluminium amalgam / tetrahydrofuran; methanol / 1.) 10 deg C, 2 h, 2.) room temperature, 4 h 4: 80 percent / K-Selectride / tetrahydrofuran / 5 h / -50 - -45 °C 5: hydrofluoric acid / acetonitrile / 1 h / -5 °C 6: base hydrolysis View Scheme

1: imidazole / dimethylformamide / 2 h / Ambient temperature 2: 95 percent / 30percent hydrogen peroxide, 3 M aq. lithium hydroxide / methanol / 5 h / -30 - -25 °C 3: aq. sodium hydrogen carbonate, aluminium amalgam / tetrahydrofuran; methanol / 1.) 10 deg C, 2 h, 2.) room temperature, 4 h 4: 80 percent / K-Selectride / tetrahydrofuran / 5 h / -50 - -45 °C 5: hydrofluoric acid / acetonitrile / 1 h / -5 °C View Scheme