water; lithium hydroxide hydrate in tetrahydrofuran T=20°C; 3 h; Inert atmosphere;

1: triethylamine / CH2Cl2 / 1 h / 0 °C 2: 777 mg / CH2Cl2 / 0.5 h / -78 °C 3: triethylamine / CH2Cl2 / 1 h / 0 °C 4: trimethylsilyl trifluoromethanesulfonate / CH2Cl2 / 1 h / -78 °C 5: 839 mg / trimethylsilyl trifluoromethanesulfonate / CH2Cl2 / 2 h / 0 °C 6: 75 percent / lithium methoxide / methanol / 14 h / 20 °C 7: 97 percent / H2O; DOWEX(R) 50WX8-200 ion-exchange resin / 3 h / Heating View Scheme