Hydrochloric Acid → HCID 19822181, compound

Participants

Reaction Steps

1.5 ml of concentrated hydrochloric acid was added to mixture of 1.1 g of 6-acetoxy-2-(4-aminophenoxymethyl)-2-isobutyl-5,7,8-trimethylchroman-4-one (prepared as described in Preparation 8) and 20 ml of acetone under a nitrogen stream and at room temperature. This was followed by 0.8 g of sodium nitrite and 0.3 ml of water, and then by 4 g of ethyl acrylate. 0.1 g of cuprous oxide was added at room temperature to the reaction mixture, which was then stirred for 1 hour. Water was then added, and the mixture was extracted with benzene. The benzene extract was washed with water and dried over anhdyrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using a 5.1 by volume mixture of hexane and ethyl acetate as eluent, to give the title compound.

Provenance & Evidence