tert-Butyl bromoacetate → Tert-butyl 3-hydroxy-3-[2-(8-phenyloctyl)phenyl]propionate

Participants

Reaction Conditions

Reaction Steps

A solution of diethylaluminum chloride (0.0082 moles, 8.2 ml) in hexane was added to a slurry of zinc dust (0.0111 mol; 0.7248 g) and a catalytic amount of copper (I) bromide (0.0004 moll; 0.0585 g) in anhydrous tetrahydrofuran (40 ml) while stirring under argon at 20° C. The resulting mixture was then cooled to -20° C. in an ice-methanol bath. A solution of t-butyl bromoacetate (0.0082 mol; 1.32 ml) and 2-(8-henyloctyl)benzaldehyde of Example 5(a) or (b) (0.0082 moles; 2.3969 g) in anhydrous tetrahydrofuran was added slowly over 60 min. The reaction was stirred overnight and was permitted to warm up slowly to room temperature. The mixture was filtered to remove zinc, concentrated, and azeotroped with methylene chloride. The resulting oil was then chromatographed on silica using 5% ethyl acetate in hexane with 0.5% formic acid to yield the desired product.

Provenance & Evidence