Ammonium Chloride → 4-t-Butyldimethylsilyloxy-3-chloro-1-(3,4-dimethoxyphenylpropyl)-1-hydroxy-2-cyclopentene

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Reaction Conditions

Reaction Steps

128 mg (5.3 mmoles) of magnesium was taken, and 4 ml of dry tetrahydrofuran was added. Then, a small amount of a solution of 1.37 g of 1-bromo-3-(3,4-dimethoxyphenyl)propane in 10 ml of dry tetrahydrofuran was added. The mixture was heated. After the initiation of the reaction, a solution of 1-bromo-3-(3,4-dimethoxyphenyl)propane in tetrahydrofuran was added little by little, and the solution was refluxed for 1.5 hours. The resulting reagent was cooled to -78° C., and a cooled solution of 1.305 g of 3-chloro-4-t-butyldimethylsilyloxy-2-cyclopentenone in dry tetrahydrofuran was added. The mixture was stirred at -78° C. for 1.5 hours. A saturated aqueous solution of ammonium chloride was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. After filtration and concentration, the residue was chromatographed on a silica gel column to give 600 mg (yield 27%) of 4-t-butyldimethylsilyloxy-3-chloro-1-(3,4-dimethoxyphenylpropyl)-1-hydroxy-2-cyclopentene.

Provenance & Evidence