Acetone → HCID 21841981, compound

Participants

Reaction Conditions

Reaction Steps

To a solution containing 6 g of the title compound of Step C dissolved in 120 mL of dichloromethane and cooled to -78° C. under a nitrogen atmosphere was added 68.4 mL of 1.0 M of diisobutylaluminum hydride. The reaction was stirred at -78° C. for 1 h, then was allowed to warm to room temperature and was stirred overnight. The reaction was then cooled to -78° C. and 10 mL of acetone was added dropwise. To this mixture at -78° C. was added 10 mL of 1N sodium hydroxide dropwise. The reaction mixture was allowed to warm to room temperature and was then poured into water, and the resulting mixture was extracted with dichloromethane. The organic extracts were washed with saturated aqueous sodium chloride, dried over magnesium sulfate and filtered. The filtrate was then evaporated to obtain 4.15 g of the title compound of Step D as a white solid melting at 117°-127° C. 1H NMR (400 MHz, CDCl3): δ 3.472 (s,3H), 3.969 (m,4H), 4.4-4.56 (m,2H), 7.19 (d,1H), 7.423 (t,1H), 7.485 (t,1H), 7.547 (d,1H).

Provenance & Evidence