Sodium hydride → HCID 14484449, compound

Participants

Reaction Steps

Sodium hydride (200 mg) was added to a mixture of the cis and trans isomers of ethyl 1-acetoxy-2-carboethoxycyclohex-4-ene (1.60 g, 7.55 mmol) in absolute ethanol (50 ml), and the mixture was stirred for 1 hour at RT. The reaction mixture was neutralized with Dowex W 50 cation exchange resin (acid form), the resin removed by filtration, the solvents removed under vacuum, and the residue chromatographed on silica gel (hexane:EtOAc 7:3, Rf=0.40) to yield 1.2 g (94%) trans 1-hydroxy-2-carboethoxycyclohex-4-ene (IR CCl4, 1732 cm-1).

Provenance & Evidence