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0 °C

To an ice cooled slurry of LiAlH4 (2.7 g) in dry ether (150 ml) was added a solution of ethyl 3-(4′-cyclopentylphenyl)-but-2-enoate (3a, 8.2 g) in dry ether (50 ml) dropwise. The mixture was stirred at 0° C. for 3 h. The reaction mixture was quenched with water (10 ml). A solution of 10% NaOH (5 ml) was added and then ether layer was decanted. The precipitate was washed with ether and combined organic layer was concentrated. The crude product was purified by column chromatography on silica gel to give 5.6 g (82.3% yield) of 3-(4′-cyclopentylphenyl)-2-butenol (4a, formula 4, R=cyclopentyl) as oil.

1. customThe reaction mixture was quenched with water (10 ml)
2. additionA solution of 10% NaOH (5 ml) was added
3. customether layer was decanted
4. washThe precipitate was washed with ether and combined organic layer
5. concentrationwas concentrated
6. customThe crude product was purified by column chromatography on silica gel