Water → HCID 57124206, compound

Participants

Reaction Steps

A mixture of 2.54 g of 6-hydroxy-2-hexanone tetrahydropyranyl ether, 2.46 g of 2,4-dihydroxy-3-propylacetophenone, 1.05 g of pyrrolidine, and 35 ml of toluene was stirred at room temperature for four days. The dark brown solution was then refluxed for 24 hours, with water removal using a Dean-Stark trap. A mixture of 1:1 ethylacetate-toluene (400 ml) and 50 g of silica were added to the reaction mixture and the slurry was stirred for 1 hour at room temperature. The silica gel was filtered with suction and washed with 1:1 ethyl acetate-toluene. The filtrate and washes were combined and concentrated in vacuo. The residual oil was purified by column chromatography on silica gel. Hexane-ethyl acetate (2:1) eluted 3.3 g (69.1%) of rac.-2,3-dihydro-2-[4-[(tetrahydro-2H-pyran-2-yl)oxy]butyl]-2-methyl-7-hydroxy-8-propyl-4H-1-benzopyran-4-one, as a dark brown oil.

Provenance & Evidence