Oxalic Acid → (RS)-2-methyl-4-methylidene-3-(2,2,2-trifluoroethyl)cyclopent-2-en-1-ol

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Reaction Steps

After 10.5 g of (RS)-2-methyl-4-methylidene-3-(2,2,2-trifluoroethyl)-1-t-butyldimethylsilyloxy-2-cyclopentene was dissolved in 50 ml of dry tetrahydrofuran, a mixture of 10.5 ml of a 1M tetrabutylammonium fluoride/tetrahydrofuran solution and 5 ml of hydrofluoric acid was added under cooling and stirred at ambient temperatures for twelve hours. The reaction solution was then added to 100 ml of an ice-cooled 5% aqueous oxalic acid, and extracted with diethyl ether (300 ml×3 times). The combined ether layer was washed successively with a saturated sodium hydrogencarbonate solution and a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the residue was treated by silica gel column chromatography (eluent: n-hexane:ethyl acetate=3:1 (v/v)) to yield 5.27 g of (RS)-2-methyl-4-methylidene-3-(2,2,2-trifluoroethyl)cyclopent-2-en-1-ol. Yield 80%

Provenance & Evidence