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

Beteiligte Stoffe

Reaktionsschritte

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 followed by dropwise addition of a solution of 2-(8-phenyloctyl)benzaldehyde (10 gm, 0.03 mole) in tetrahydrofuran (25 ml). 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 solution 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) δ 1.29-1.52 (12H,m) 2.52-2.78 (6H,m) 5.39 (1H,dd) 7.10-7.60 (9H,m).

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