Pyridine → Isobutyric acid 4-(tert-butyl-dimethyl-silanyloxy)but-2-enyl ester

Participants

Reaction Steps

A solution of 60% NaH (2.27 g, 56.75 mmoles) in tetrahydrofuran (15 mL) was cooled to 0° C. and to the solution cis-2-butene-1,4-diol (5.0 g, 56.75 mmoles) in tetrahydrofuran (10 mL) was added. The reaction was stirred at room temperature for thirty minutes and tert-butyl-chloro-dimethyl-silane (8.56 g, 56.75 mmoles) in tetrahydrofuran (15 mL) was added and stirred for another two hours. The reaction was quenched with 10% NH4Cl and extracted with ethyl acetate. The organic layer was washed with brine (30 mL), dried with MgSO4, filtered, and evaporated in vacuo. The crude oil was purified by flash column chromatography (hexanes:ethyl acetate 100:0 to 50:50). The resulting product was dissolved in dichloromethane (25 mL) and pyridine (3.95 g, 50.6 mmoles) and isobutyryl chloride (2.68 g, 25.3 mmoles) were added. Then, the solution was stirred at room temperature for twelve hours. The reaction was quenched with water and extracted with dichloromethane. The organic layer was washed with water (50 mL), dried with MgSO4, filtered and evaporated in vacuo. The solvent was evaporated in vacuo and the product was purified by flash column chromatography (hexanes:ethyl acetate 100:0 to 70:30) to provide the title compound as a colorless oil.

Provenance & Evidence