Dimethyl Sulfoxide → HCID 19761001, compound

Participants

Reaction Steps

A solution of 1.58 ml of dimethyl sulphoxide in 10 ml of methylene chloride was added dropwise at -60° during 5 minutes to a solution of 0.8 ml of oxalyl chloride in 30 ml of methylene chloride. After stirring for 2 minutes a solution of the crude 1-[4-[[6-(diethylamino)hexyl]oxy]phenyl]-3-phenylpropanol in 20 ml of methylene chloride was added thereto at -60° within 10 minutes. After 15 minutes 7.5 ml of triethylamine were added thereto at -60° and the reaction mixture was left to warm to room temperature. After one hour at room temperature 100 ml of water were added thereto, the organic phase was separated and the aqueous phase was extracted twice with 100 ml of methylene chloride each time. The combined organic phases were dried over magnesium sulphate and evaporated. After chromatogrpahy of the residue on 240 g of silica gel with ammonium hydroxide/methanol/methylene chloride (1:10:90 ) there were obtained 1.76 g (37%) of 4'-[[6-(diethylamino)hexyl]oxy]-3-phenylpropiophenone as a yellow oil which crystallizes upon standing; m.p. 83°-84°.

Provenance & Evidence