Methanesulfonyl chloride → HCID 86673332, compound

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Reaction Steps

To a solution of 5-formyl-2-thiophencarboxylic acid tert-butyl ester (5 g, 23.6 mmol) in tetrahydrofuran (50 mL) and methanol (5 mL), was added sodium borohydride (0.50 g, 13.0 mmol) at 0° C., and the mixture was stirred for 2 hours at room temperature. The reaction mixture was partitioned between ethyl acetate and 0.5N-hydrochloric acid solution. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was dissolved in dichloromethane (100 mL), methanesulfonyl chloride (1.9 ml, 24 mmol) and diisopropylethylamine (5.7 ml, 33 mmol) were added at 0° C., and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, 0.5N-hydrochloric acid solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound (5.3 g, 23 mmol).

Provenance & Evidence