Water → 2,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonate

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Reaction Steps

2-Trimethylsilylethyl carbonochloridate (4.8 g, 26.9 mmol) was taken up in dry acetronitrile (50 mL). The solution was cooled to 0° and solid N-hydroxysuccinimide (4.0 g, 34.8 mmol) was added with vigorous stirring followed by a solution of dry triethylamine (3.2 g, 31.6 mmol) in dry acetonitrile (5 mL). The mixture was stirred at low temperature for 15 minutes, then at room temperature overnight. The mixture was poured into water (200 ml) and extracted with ether (4×50 mL). The organic extracts were combined, washed with water (2×60 mL), 1 normal hydrochloric acid (60 mL), again water (60 mL), brine (60 mL), dried with magnesium sulfate and evaporated to dryness. The residue was taken up in boiling hexane (200 mL) and the solution allowed to cool. Crystallization was completed by storage at −15° C. (yield: 1.70 g).

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