1-Pentene → 1-(5-(Hex-2-enyl)benzo[d][1,3]dioxol-2-yl)ethanone

Participants

Reaction Steps

A solution of 1-(5-allylbenzo[d][1,3]dioxol-2-yl)ethanone (5 g), phenylmethylenebis(tricyclohexylphosphine) ruthenium dichloride (0.9 g) and pent-1-ene (5 g) in dichloromethane (40 ml) was stirred at room temperature. After 2 hours, a control by gc analysis shows 60% conversion, but three additional portions of 5 g of pent-1-ene were added during the reaction time (48 hours) to go to completion. Then, the reaction mixture was filtered on a short column of silica gel and concentrated in vacuum to remove the solvent. Finely the crude product was purified by flash chromatography on silica gel (eluant heptane/ethyl acetate 95/5) to give 0.8 g (19%) of a colorless oil, identified as a 85/15 E/Z mixture.

Provenance & Evidence