Imidazole → (Z)-4-((tert-butyldimethylsilyl)oxy)but-2-en-1-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of cis-1,4-butene diol (6) (20.0 g, 227.27 mmol) in dry CH2Cl2 (700 mL) at 0° C. was added imidazole (23.21 g, 340.91 mmol) and tert-butyldimethylsilyl chloride (37.68 g, 250.0 mmol). The reaction mixture was stirred at 0° C. for 6 h. After completion of reaction (monitored by TLC), it was diluted with CH2Cl2 (500 mL) washed with water, brine and dried over anhydrous Na2SO4. Removal of solvent under reduced pressure gave the crude product which was then purified by column chromatography with petroleum ether/EtOAc (9:1 v/v) to give (7) as a colorless liquid.

Provenance & Evidence