Hexane → HCID 13552982, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Compound 3b (0.5 mmol) in tetrahydrofuran (2 mL) at -78° C. under nitrogen was added n-butyllithium in hexane (0.5 mmol). After 30 minutes, a solution of N- formylpiperidine (0.55 mmol) in tetrahydrofuran (0.5 mL) was added dropwise at -78° C. The reaction mixture was stirred for 5 hours while allowing it to warm to -10° C. The reaction was quenched with saturated aqueous ammonium chloride (1 mL) and diluted with diethyl ether (10 mL). The aqueous phase was extracted with diethyl ether (2×10 mL) and the combined organic phases were washed with saturated aqueous ammonium chloride (3×5 mL) and brine and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue purified by flash chromatography on silica gel eluted with ethyl acetate:hexane (2:98) to afford Compound 3c as an oil (Rf =0.2).

Provenance & Evidence