Sodium hydride → 1-[1-(2,2-Diethoxyethoxyl)but-3-en-1-yl]-1-methylcyclopropane

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Reaction Steps

A solution of 1-(1-methylcyclopropyl)but-3-en-1-ol (C52) (6.0 g, 47.6 mmol) in tetrahydrofuran (50 mL) was added to a 0° C. suspension of sodium hydride (60% in mineral oil, 7.7 g, 190.5 mmol) in tetrahydrofuran (200 mL). After stirring at room temperature for 10 minutes, 2-bromo-1,1-diethoxyethane (97%, 37.5 g, 190.5 mmol) was added drop-wise at room temperature. The reaction mixture was heated to 75° C. for 24 hours. It was then cooled to 0° C., slowly quenched with water (200 mL) and extracted with dichloromethane (3×500 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo; purification via silica gel chromatography (Gradient: 0% to 10% ethyl acetate in petroleum ether) afforded the product as a yellow oil.

Provenance & Evidence