thionyl chloride T=-10 - 20°C; 2 h; Inert atmosphere;

in diethyl ether

1: 15 g / diethyl ether 2: 35 percent / sodium ethoxide / toluene / 1 h / Heating View Scheme

1: 15 g / diethyl ether 2: 35 percent / sodium ethoxide / toluene / 1 h / Heating 3: diethyl ether / 1 h / Ambient temperature 4: 1.) sodium dihydrobis(2-methoxyethoxy)aluminate, 2.) 25percent HAc / 1.) THF, -20 deg C, 0.5 h, 2.) room temp., 8 h View Scheme