Hydroquinone → HCID 69853448, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-benzyl-5-(3-ethoxycarbonyl-allyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (6.55 g) in toluene (50 ml) was placed in a stainless steel bomb equipped with a PTFE liner. Hydroquinone (350 mg) was added, and the vessel cooled to −78° C. 1,3-butadiene (100 g) was condensed into the vessel, which was then sealed and heated to 150° C. for 16 hours. After cooling, the vessel was opened and the contents removed and evaporated to dryness. The residue was subjected to flash chromatography on silica gel eluting with hexane/ethyl acetate (95:5) to afford 4-benzyl-5-(6-ethoxycarbonyl-cyclohex-3-enylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (2.54 g, 34%) as a mixture of trans isomers (mass spectrum 458 [M+H]+) together with recovered starting material (2.17 g, 33%).

Provenance & Evidence