Hexane → 1-(6-Isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinolin-8-yl)-ethanone

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Reaction Conditions

Reaction Steps

To a solution of a 1.6 M solution of n-butyl lithium in hexane (3.33 ml, 5.33 mmol) and 20 ml of anhydrous THF under argon at −78° C. was slowly added triethyl-2-fluoro-2-phosphonoacetate (1.29 g, 5.33 mmol). After 40 minutes at −78° C., a solution of 1-(1-ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-ethanone (Intermediate 12, 497 mg, 1.33 mmol) in 4 ml THF was added by cannula. The resulting mixture was stirred at −78° C. for 10 minutes, allowed to warm up to room temperature, and then heated to 80° C. for 12 hours. The reaction was quenched with saturated NH4Cl and product was extracted with ethyl ether. The extract was washed with water, and brine, dried over Na2SO4, concentrated in vacuo, and the residue was purified by column chromatography using 2% ethyl acetate in hexane to yield the title compound as a yellow oil.

Provenance & Evidence