Hydrochloric Acid → HCID 19822223, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 13 g of ethyl 3-[4-(6-t-butoxycarbonylmethoxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)phenyl]-2-chloropropionate (prepared as described in Preparation 64), 2.6 g of thiourea and 15 ml of sulfolane was heated under a nitrogen stream at 120°-130° C. for 5 hours. 30 ml of 2N aqueous hydrochloric acid and 60 ml of 2-methoxyethanol were added to the resulting mixture, which was then heated at 110° C. for 3 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled from the dried extract, and the residue was purified by silica gel column chromatography (eluted with a 4:1 by volume mixture of benzene and ethyl acetate) to give the title compound.

Provenance & Evidence