Diisopropylamine → Tert-butyl 3-hydroxy-3-[2-(8-phenyloctyl)phenyl]propionate

Participants

Reaction Steps

A solution of diisopropylamine (4.8 ml, 0.03 mole) in tetrahydrofuran/hexane (100 ml, 1/1) was cooled to -60° C. and n-butyllithium (2.5M solution in hexane, 13.6 ml, 0.03 mole) was added. This solution was stirred for 10 minutes followed by addition of t-butyl acetate (4.6 ml, 0.03 mole). The mixture was stirred for an additional 10 minutes before addition of a solution of 2-(8-phenyloctyl)benzaldehyde (10 gm, 0.03 mole) in tetrahydrofuran (25 ml) was added dropwise. The whole was stirred first for 30 minutes at -50° C. and then for 30 minutes at -20° C. The reaction, mixture was poured into aqueous acid and extracted twice with diethyl ether. The combined extracts were washed with 5% aqueous sodium bicarbonate solution and saturated aqueous sodium chloride sodium and then dried over anhydrous magnesium sulfate, filtered and evaporated. Chromatography on silica gel using hexane-ethyl acetate (95/5) to elute gave the product as an oil. 90 MHz NMR (CDCl3) δ1.29-1.52 (12 H,m) 2.52-2.78 (6 H,m) 5.39 (1 H,dd) 7.10-7.60 (9 H,m).

Provenance & Evidence