Tetrahydrofuran → (1RS,4RS)-4-allyl-4-hydroxy-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether

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Reaction Steps

To a solution mixture of 3.5 g of (RS)-4-oxo-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether obtained according to the method described in Org. Syn., Vol 73, p. 36 and 35 ml of tetrahydrofuran was added under nitrogen stream and at 0° C. 11 ml of 2.0 M diethyl ether solution of allylmagnesium chloride and the resulting mixture was stirred at the same temperature for 1 hour. Then the reaction liquid was poured into ice-cooled saturated aqueous ammonium chloride solution and extracted two times with diethyl ether. The combined 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 residue thus obtained was subjected to silica gel column chromatography to obtain 4.1 g of (1RS,4RS)-4-allyl-4-hydroxy-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether. Yield 98%

Provenance & Evidence