Water → HCID 57771552, compound

Participants

Reaction Steps

To a suspension of lithium aluminum hydride (250 mg) in diethyl ether (20 mL) was added dropwise a solution of 4,4-dimethyl-3-pent-4-enyl-cyclohex-2-enone (1.05 g) obtained in Step 2 in diethyl ether (5 mL) under ice-cooling and nitrogen atmosphere, followed by stirring the reaction mixture under ice-cooling for 30 minutes. Then, after successive dropwise addition of water (0.25 mL), 4N aqueous sodium hydroxide solution (0.25 mL) and water (0.75 mL), the reaction mixture was stirred at room temperature for 30 minutes. After the resulting insolubles were filtered off, the filtrate was concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=15:1 to 10:1) to give 4,4-dimethyl-3-pent-4-enyl-cyclohex-2-enol (830 mg).

Provenance & Evidence