Allyl Alcohol → HCID 15598953, compound

Participants

Reaction Steps

17.45 g of a 55% w/w suspension of sodium hydride in mineral oil were suspended in 400 ml of toluene; to the resulting suspension were added 400 ml of allyl alcohol, whilst ice-cooling and under a nitrogen atmosphere. 122.93 g of methyl (E)-3-(5-benzyloxy-1H-indol-3-yl)acrylate were added thereto, and the mixture was heated under reflux for 10 minutes. The reaction mixture was then washed, in turn, with a saturated aqueous solution of citric acid, with a saturated aqueous solution of sodium hydrogen carbonate, with water and with a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. It was then condensed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography using 20% v/v ethyl acetate in hexane as eluent, to give 100.12 g of the title compound as crystals melting at 73°-77° C.

Provenance & Evidence