Water → HCID 86704607, compound

Participants

Reaction Steps

To a 0° C. solution of 2-iodo-4-(4-methoxyphenyl)cyclohexanone (Step A) (363 mg, 1.099 mmol) in diethyl ether (3 ml), under nitrogen, was added sodium methoxide (77 mg, 1.429 mmol) and the resulting mixture was stirred at RT for 30 minutes. Water was added and extracted 2 times with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc in hexanes to afford the titled compound. 1H NMR (500 MHz, CDCl3): δ 7.15 (d, J=8.6 Hz, 1H); 6.84 (d, J=8.6 Hz, 1H); 3.79 (s, 3H); 3.70 (s, 3H); 3.17 (p, J=8.6 Hz, 1H); 3.06-2.91 (m, 1H); 2.34 (ddd, J=13.2, 8.1, 4.7 Hz, 1H); 2.19-2.06 (m, 2H); 2.03-1.80 (m, 2H); 1.70-1.58 (m, 1H).

Provenance & Evidence