Diethyl Ether → HCID 10465705, compound

Participants

Reaction Steps

A solution of the dimethyl acetal of p-anisaldehyde (5.3 g) in dry diethyl ether (90 mL) at 0° was treated with a 1.7 molar solution of t-butyl lithium (20.5 mL). The solution was stirred for 1.5 h at 0°, followed by addition of anhydrous dimethylformamide (2.9 mL). The solution was allowed to warm to 23° over 1 h, quenched by the addition of water, and extracted with ethyl acetate (2×200 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 (2.63 g).

Provenance & Evidence