HCID 13924131, compound → (3aR,7aS)-4,4,7a-trimethyl-3a,5,6,7-tetrahydro-3H-1-benzofuran-2-one

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Reaction Steps

Compound (13) (1.00 g, 5.55 mmoles) was dissolved in dry acetic acid, and platinum oxide (0.10 g) was added to the solution. The mixture was shaken for 23 hours under hydrogen pressure (30 atms.). The catalyst was separated by filtration, and the filtrate was concentrated under vacuum. The residue was diluted with ethyl acetate, and the ethyl acetate solution was washed with an aqueous solution of sodium hydrogen-carbonate, water and an aqueous solution of sodium chloride in this order, dried over magnesium sulfate, and concentrated under vacuum. The residue was purified by column chromatography (10 g of silica gel; n-hexane/ethyl acetate) to give crystalline (3aR,7aS)-isomer (14) (0.910 g, yield 80%). Recrystallization from n-hexane gave 0.669 g of the purified compound (14).

Provenance & Evidence