4-Toluenesulfonyl chloride → 2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

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Reaction Steps

To a solution of (2,2-dimethyl-1,3-dioxolan-4-yl)methanol (5.28 g, 40.0 mmol), triethyl amine (12.12 g, 120.0 mmol) and 4-dimethylaminopyridine (500 mg, 4.0 mmol) in dichloromethane (200 mL) was added tosyl chloride (15.2 g, 80.0 mmol). The reaction mixture was stirred at RT overnight, then quenched with water (200 mL) and extracted with ethyl acetate. The organic layers were separated, combined, washed with water (200 mL) and brine (200 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography, eluting with ethyl acetate/petroleum ether=1/8, to afford (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate (6.1 g, yield 53%), MS (ES+) C13H18O5S requires: 286, found: 287 [M+H]+.

Provenance & Evidence