Sodium hydride → 3-(3,3-Diethoxypropoxy)-2-methylprop-1-ene

Participants

Reaction Steps

To a stirred solution of 3,3-diethoxy-1-propanol (3.0 g, 22.2 mmol) in anhydrous THF (50 mL) was added sodium hydride (60% dispersion in mineral oil, 1.07 g, 26.6 mmol). The reaction mixture was stirred for 30 minutes, and 3-bromo-2-methyl-1-propene (3.63 g, 24.5 mmol) then added. The reaction mixture was then stirred for a further 18 hours. The reaction mixture was quenched with saturated sodium hydrogen carbonate and extracted with ethyl acetate (×3). The combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution and brine, dried (sodium sulfate), filtered and concentrated under reduced pressure to afford an oil (2.25 g, 50%). The material used in the next step without further purification.

Provenance & Evidence