Ethyl formate → HCID 67113927, compound

Participants

Reaction Steps

Under an argon atmosphere, ethyl formate (110.6 μL, 1.33 mmol, 5 eq) then sodium methoxide (71.7 mg, 1.33 mmol, 3 eq) were successively added to a solution of 31 (75 mg, 0.265 mmol) in dry benzene (3.07 mL). This mixture was stirred at room temperature for 1 hour, during which time a color change from orange to red-brown occurred. The mixture was then diluted with a mixture of methylene chloride/ethyl ether (1:2, 20 mL) and washed with saturated aqueous ammonium chloride solution (2×8 mL). The aqueous washings were combined and extracted with methylene chloride/ethyl ether (1:2, 3×10 mL). The organic layers were then combined and washed with brine (1×10 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to give 4-benzyl-6-hydroxymethylene-4-((trimethyl-silyl)ethynyl)cyclohex-2-enone (83 mg, 100%) as a yellow-brown oil. The product was used in the next reaction without further purification: 1H NMR (CDCl3) δ 13.67 (1H, bs), 7.45 (1H, bs), 7.23-7.16 (5H, m), 6.51 (1H, dd, J=1, 10.5 Hz), 5.98 (1H, d, J=10 Hz), 2.84 (1H, d, J=13 Hz), 2.68 (1H, d, J=13 Hz), 2.57 (1H, dd, J=1, 14.5 Hz), 2.40 (1H, d, J=15 Hz); 13C NMR (CDCl3) δ 187.5, 168.7, 151.4, 136.0, 130.8, 128.5, 128.1, 127.2, 127.1, 109.9, 108.0, 44.4, 38.9, 34.6, 0.10.

Provenance & Evidence