Triethylamine → 5-(tert-Butyl-dimethyl-silyloxy)-4-hydroxy-pentanoic Acid Ethyl Ester

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Reaction Steps

A solution of 4,5-dihydroxy-pentanoic acid ethyl ester, (7 g, 43.2 mmol) and 4-dimethylaminopyridine (0.2 g, 1.73 mmol) in dichloromethane (145 mL) at room temperature under nitrogen is treated with tert-butyl-dimethyl-silyl chloride (7.8 g, 51.85 mmol) and triethylamine (6.9 mL, 47.52 mmol) and stirred 18 h. The mixture is diluted with dichloromethane (100 mL), washed with water (100 mL), saturated ammonium chloride solution, and brine. The solution is filtered and concentrated in vacuo to yield the title compound, 11.85 g (99%), as a colorless oil.

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