Aluminium lithium hydride → HCID 14827124, compound

Participants

Reaction Steps

Methyl cis-2-benzoyloxy-cyclohex-4-enecarboxylate (6, 1.1 g, 4.19 mmol) was dissolved in THF (10 ml), and the solution added to a dispersion of lithium aluminum hydride (0.35 g, 9.15 mmol) in THF (30 ml) at -78° C. The mixture was warmed to RT and stirred for 5 hours. The reaction mixture was then cooled to -15° C., and then diluted successively with water (0.35 ml), 15% NaOH (0.35 ml), and water (1.05 ml). The precipitate was removed by filtration, washed with EtOAc, and the solvent removed under vacuum. The residual oil was purified by chromatography on silica gel (EtOAc, Rf=0.28) to yield cis 2-hydroxymethylcyclohex-4-eneol (7, 419 mg, 78%) as a colorless oil.

Provenance & Evidence