Water → Ethyl 2-(oxan-4-ylidene)acetate

Participants

Reaction Conditions

Reaction Steps

Triethyl phosphonoacetate (22.6 g, 99.88 mmol) was added to a solution of dihydro-2H-pyran-4(3H)-one (10.0 g, 99.88 mmol) in DMF (100 ml) at room temperature, and the mixture was stirred at 80° C. for 15 hr. The mixture was allowed to cool to room temperature, was diluted with water, and was extracted with ether. The organic layer was washed with water and saturated brine, was dried over anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate=95:5) to give the title compound as a yellow oil (13.2 g, yield 78%).

Provenance & Evidence