Acetone → HCID 14329882, compound

Participants

Reaction Steps

A mixture of 1.2 g (3.23 mmoles) of racemic-7-[(5-bromopentyl)oxy]-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid ethyl ester, 1.0 g (5.15 mmoles) of 2',4'-dihydroxy-3'-propylacetophenone, 1.8 g (13.0 mmoles) of anhydrous potassium carbonate, 30 ml of acetone, and 15 ml of N,N-dimethylformamide was stirred and refuxed for 6 hr. After being cooled, the mixture was diluted with ether. The ether phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue (2.1 g) was chromatographed on 50 g of silica gel. Elution with 19:1 toluene-ethyl acetate afforded 1.3 g (83%) of racemic-7-[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyloxy]-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid ethyl ester as a yellow oil.

Provenance & Evidence