Hydrochloric Acid → HCID 53996178, compound

Participants

Reaction Steps

A mixture of 335 mg of racemic-6-acetyl-7-(3-bromopropoxy)-3,4-dihydro-2-methyl-8-n-propyl-2H-1-benzopyran-2-propanoic acid ethyl ester, 143 mg of 2',4'-dihydroxy-3'-n-propylacetophenone, 217 mg of anhydrous potassium carbonate, 6 ml of anhydrous acetone, and 3 ml of anhydrous N,N-dimethylformamide was stirred and refluxed for 17 hours. An additional 100 mg of potassium carbonate was added and stirring, and refluxing were continued for 4 hours. After being cooled to room temperature, the mixture was cautiously acidified to pH 1 by the addition of 1N hydrochloric acid. Water was added and the mixture was worked-up with ether in the usual manner. The residue was chromatographed on 50 g of silica gel. Elution with 9:1 toluene-ethyl acetate afforded 219 mg (52.6%) of racemic-6-acetyl-7-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)propoxy]-3,4-dihydro-2-methyl-8-n-propyl-2H-1-benzopyran-2-propanoic acid ethyl ester as a yellow oil.

Provenance & Evidence