Hydrochloric Acid → Methyl 4-(1-diphenylmethoxycarbonylcyclopropyl)-2,3,5,6-tetrafluorobenzoate

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Reaction Steps

In 330 ml of N,N-dimethylformamide was suspended 3.7 g of 60% sodium hydride. To the resulting suspension was added 20.2 g of trimethylsulfoxonium iodide with ice-cooling. The resulting mixture was stirred at room temperature for 1 hour. Thereto was added 33.0 g of methyl 4-(1-diphenylmethoxycarbonylvinyl)-2,3,5,6-tetrafluorobenzoate. The resulting mixture was stirred at the same temperature for 2 hours. To the reaction mixture were added 300 ml of ethyl acetate and 900 ml of water in this order. The resulting mixture was adjusted to pH 1 with 2N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue obtained was purified by a column chromatography (eluant: toluene) to obtain 22.5 g (yield: 66.1%) of methyl 4-(1-diphenylmethoxycarbonylcyclopropyl)-2,3,5,6-tetrafluorobenzoate.

Provenance & Evidence