1: 1.) sodium hydride / 1.) 0 deg C, 0.5 h, 2.) room temperature, 20 h 2: 95 percent / hydrogen / 10percent palladium on charcoal / ethyl acetate / 7 h 3: sodium/potassium alloy / tetrahydrofuran / 1 h / -10 - -5 °C / 0 Torr 4: 55 percent / methanol View Scheme

1: 95 percent / hydrogen / 10percent palladium on charcoal / ethyl acetate / 7 h 2: sodium/potassium alloy / tetrahydrofuran / 1 h / -10 - -5 °C / 0 Torr 3: 55 percent / methanol View Scheme

1: tetrahydrofuran / -78 °C 2: 1.) sodium hydride / 1.) 0 deg C, 0.5 h, 2.) room temperature, 20 h 3: 95 percent / hydrogen / 10percent palladium on charcoal / ethyl acetate / 7 h 4: sodium/potassium alloy / tetrahydrofuran / 1 h / -10 - -5 °C / 0 Torr 5: 55 percent / methanol View Scheme

in methanol

1: sodium/potassium alloy / tetrahydrofuran / 1 h / -10 - -5 °C / 0 Torr 2: 55 percent / methanol View Scheme

aluminium trichloride T=-5 - 0°C; 0.5 h;

fluorosulfonic acid methyl ester 20 h; Ambient temperature; Yield given. Yields of byproduct given;