Diethyl Ether → HCID 10443088, compound

Participants

Reaction Steps

A solution of the dimethyl acetal of m-anisaldehyde (490 mg) in dry diethyl ether (10 mL) at 0° was treated with a 1.7 molar solution of t-butyllithium (1.75 mL). The solution was stirred for 1 h at 0°, followed by addition of anhydrous dimethylformamide (0.25 mL). The solution was allowed to warm to 23° over 15 h, quenched by the addition of water, and extracted with ethyl acetate (2×50 mL). The combined organic layers were dried (MgSO4) and evaporated. The residue was purified by chromatography on silica using 90% hexane-ethyl acetate as eluent to afford the title compound as a pale yellow oil (255 mg).

Provenance & Evidence