Benzaldehyde → HCID 70377050, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of the compound of Example 17(a) (1.4 g, 4.5 mmoles) and tetrahydrofuran (15 ml) under argon was cooled to -78° C. with a dry ice acetone bath. A 2.6 M solution of n-butyllithium in hexane (3.55 ml, 9 mmoles) was added dropwise. The resulting red-orange solution was stirred at -78° C. for 30 minutes. Hexamethylphosphoramide (5.5 ml) was added in one portion followed by benzaldehyde (0.41 ml, 4 mmoles) in tetrahydrofuran (5 ml). The reaction mixture was stirred under argon for 30 minutes. The tetrahydrofuran was evaporated and the residue was dissolved in ether and washed with cold 3 N hydrochloric acid. The combined organic phase was dried over magnesium sulfate, filtered and evaporated. The crude material was then chromatographed on silica gel eluted with 4% ethyl acetate in hexane plus 1% formic acid to yield the desired compound.

Provenance & Evidence