Hydrochloric Acid → HCID 15671158, compound

Participants

Reaction Steps

Following a procedure similar to that described in Preparation 4, 0.8 g of 7-acetoxy-6-acetyl-2,8-dimethyl-2-(4-nitrophenoxymethyl)-4-oxochroman (prepared as described in Preparation 22) was hydrogenated by using 0.2 g of 10% w/w/ palladium-on-carbon, 8 ml of methanol and 1 ml of benzene. The product was then reacted with 135 mg of sodium nitrite, 0.6 ml of concentrated aqueous hydrochloric acid, 1.6 ml of ethyl acrylate, 30 mg of cuprous oxide, 6 ml of acetone and 0.5 ml of water, following a procedure similar to that described in Preparation 5, to give the title compound in admixture with its 7-acetoxy compound in a ratio of about 1:1. The mixture was subjected to silica gel column chromatography eluted with a 10:1 by volume mixture of benzene and ethyl acetate, to afford the title compound as a pale yellow oily substance.

Provenance & Evidence