Tetrabutylammonium Fluoride → HCID 12952598, compound

Participants

Reaction Steps

3 To a solution of (RS)-2-methyl-4-methylidene-3-(2-propenyl)-1-tert-butyldimethyl-silyloxycyclopent-2-ene (1.0 g, obtained above) in dry tetrahydrofuran (10 ml) was added a tetrahydrofuran solution (5.7 ml) of 1M tetrabutylammonium fluoride under ice-water cooling. The solution was then stirred at room temperature for 12 hours. The reaction solution was poured into ice-water, and extracted with ether (100 ml×2). The ether layers were combined and washed with brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resultant residue was subjected to silica gel column chromatography (eluent; n-hexane: ethyl acetate=3:1) to afford the desired product (RS)-2-methyl-4-methylidene3-(2-propenyl)cyclopent-2-ene-1-ol (460 mg, yield 82.3%) as a pale yellow oil.

Provenance & Evidence