Vinyl chloroformate → HCID 67915896, compound

Participants

Reaction Steps

A solution of (3aRS,7aRS)-2-benzyl-7,7-bis(3-tolyl)perhydro-4-isoindolone (13.7 g) in 1,2-dichloroethane (150 cc) is treated with vinyl chloroformate (3.7 cc) and heated to reflux for 3 hours, then concentrated under reduced pressure (2.7 kPa). The residue is chromatographed on silica gel (particle size 0.04-0.063 mm, column 5.4 cm in diameter and 39 cm high), eluting under a nitrogen pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (80:20). Fractions 23 to 39 are combined and concentrated to dryness under reduced pressure (2.7 kPa) to give (3aRS,7aRS)-7,7-bis(3-tolyl)-2-vinyloxycarbonylperhydro-4-isoindolone (7.4 g) in the form of a white meringue-like product.

Provenance & Evidence