2-(Trimethylsilyl)ethanol → 5-Methyl-thiophene-2-carboxylic acid 2-trimethylsilanylethyl ester

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Reaction Steps

A solution of 5-Methyl-thiophene-2-carboxylic acid (23.58 g, 166 mmol) in MeCN (300 mL) is treated with EDCl (33.41 g, 174 mmol) and DMAP (2.03 g, 16 mmol). The mixture is stirred for 5 min and 2-(trimethylsilyl)ethanol (19.61 g, 166 mmol) is added. The mixture is stirred at RT for 16 h and the solvent is evaporated. The residue is partitioned between EtOAc and water. The organic layer is diluted with an equal portion of hexane and dried over anhydrous MgSO4. The solution is passed through a plug of silica gel and the solvents are evaporated to dryness to give 5-methyl-thiophene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester as a clear oil.

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