4-Toluenesulfonyl chloride → (2-Methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(1-tosyloxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate

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Reaction Steps

To a solution of 97 mg (0.20 mmol) of (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(1-hydroxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate obtained in Example 3 and dissolved in 0.5 ml of diethyl ether and 0.5 ml of DMF, 12 mg (0.25 mmol) of sodium hydride and 39 mg (0.20 mmol) of p-toluenesulfonyl chloride were added, and the mixture was stirred overnight at room temperature. After an addition of 1 ml of a saturated ammonium chloride aqueous solution, the mixture was extracted with diethyl ether (2 ml×3 times). The extract was dried over anhydrous magnesium sulfate, then filtered and concentrated under reduced pressure to obtain a crude produce. The crude product was purified by thin layer chromatography (silica gel, dichloromethane/hexane=1/3) to obtain 83 mg of (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(1-tosyloxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate as a colorless oily substance.

Provenance & Evidence