Imidazole → Diethyl 3-(tert-Butyldimethylsilyloxy)glutarate

Participants

Reaction Steps

To a solution of imidazole (40.85 g, 600 mmole) in dry CH2Cl2 (300 ml) was added dropwise a solution of t-butyldimethylsilyl chloride (45.2 g, 300 mmole) in dry CH2Cl2 (100 ml). After 15 minutes, the solution was treated dropwise over a 40 minute period with a solution of diethyl 3-hydroxyglutarate (40.8 g, 200 mmole) in CH2Cl2 (100 ml). After stirring at room temperature under argon for 18 hours, the mixture was washed with water and saturated NaCl solution, dried over Na2SO4 and evaporated. The crude product (73.04 g) was purified by chromatography on Merck silica gel (4000 ml), eluting with ethyl ether-hexane (1:9) to give title compound (~65 g, theory 63.6) as a colorless oil.

Provenance & Evidence