ETHYL 8-(2-NAPHTHYL)-8-OXOOCTANOATE → HCID 11809077, compound

Participants

Reaction Steps

To a solution of methyltriphenylphosphonium bromide (469 mg,1.31 mmol) in THF (6 mL) pre-cooled to 0° C. under nitrogen atmosphere was added dropwise n-butyllithium (1.42M solution in hexanes, 905 μL, 1.28 mmol) and stirred over 20 minutes. To this a THF (4mL) solution of 49g (82 mg, 0.262 mmol) was transferred via cannula. The yellow mixture was stirred over 30 minutes and quenched with a saturated aqueous solution of ammonium chloride, as the yellow color immediately disappeared. The solvent was removed by evaporation in vacuo and the aqueous residue was partitioned between water and ethyl acetate. The aqueous layer was then extracted with ethyl acetate and the combined organic layers were washed with brine, dried (MgSO4) and concentrated. The crude residue was purified by flash chromatography (5% to 8% diethyl ether in hexane) to afford the title compound 168 (43 mg) in 52% yield. 1H NMR: (CDCl3) δ: 7.85-7.78 (m, 4H), 7.58 (dd, J=8.8, 1.9 Hz, 1H), 7.48-7.44 (m, 2H), 5.42 (d, J=1.1 Hz, 1H), 5.16 (d, J=1.4 Hz, 1H), 4.12 (q, J=7.1 Hz, 2H), 2.62 (t, J=6.9 Hz, 2H), 2.28 (d, J=7.4 Hz, 2H), 1.64-1.49 (m, 4H), 1.39-1.33 (m, 4H), 1.25 (t, J=7.1 Hz, 3H). MS (ESI)=311 (MH+).

Provenance & Evidence