Tetrabutylammonium Fluoride → (RS)-3-allyl-4-methyl-3-cyclopenten-1-ol

Participants

Reaction Steps

To a solution of 2 g of (RS)-3-allyl-4-methyl-3-cyclopenten-1-yl (t-butyldimethylsilyl) ether in 20 g of tetrahydrofuran was added under ice-cooling 16 ml of 1 M tetrahydrofuran solution of tetrabutylammonium fluoride, and the resulting mixture was stirred at room temperature for 6 hours. Then the reaction liquid was poured into ice water and extracted with diethyl ether. The ether layer was washed with saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The oily substance thus obtained was subjected to silica gel column chromatography to obtain 0.58 g of (RS)-3-allyl-4-methyl-3-cyclopenten-1-ol. Yield 53%

Provenance & Evidence