Tetrahydrofuran → ethyl rel-(1R,2S)-4-[1-(5-chloropyrimidin-2-yl)ethenyl]-2-methylcyclohexanecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyltriphenylphosphonium bromide (2.22 g, 6.20 mmol) in THF (22 mL) was added sodium hydride (0.24 g, 6.2 mmol, 10 wt %) at 0° C. After being stirred at 25° C. for 3 hours, ethyl rel-(1R,2S)-4-[(5-chloropyrimidin-2-yl)carbonyl]-2-methylcyclohexanecarboxylate (0.62 g, 2 mmol) was added in one portion at 0° C. The reaction mixture was stirred at 20° C. for 6 hours and then saturated aqueous ammonium chloride was added. The reaction mixture was extracted with ethyl acetate, and the combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by prep-TLC (ethyl acetate/petroleum ether) to give ethyl rel-(1R,2S)-4-[1-(5-chloropyrimidin-2-yl)ethenyl]-2-methylcyclohexanecarboxylate. MS ESI calc'd for C16H22ClN2O2[M+H]+ 309. found 309. 1H NMR: (400 MHz, CD3OD) δ 8.80-8.74 (m, 2H), 6.45-6.40 (m, 1H), 5.55-5.49 (m, 1H), 4.19-4.12 (m, 2H), 2.72-2.47 (m, 2H), 1.87-1.74 (m, 3H), 1.73-1.58 (m, 2H), 1.31-1.25 (m, 4H), 1.22-1.18 (m, 1H), 1.04-1.00 (m, 3H).

Provenance & Evidence