反应详情

To a suspension of triphenyl-(3-ethoxycarbonylpropyl)phosphonium bromide (2.27 g, 5 mmol) and 5-methylfurfural (0.55 g, 5 mmol) in 5 mL of dry tetrahydrofuran, a 1 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (5 mL) was added dropwise. The reaction mixture was stirred at room temperature for 2 hours and quenched with 2 N hydrochloric acid solution. The reaction mixture was extracted with ethyl acetate and the combined organic layers were dried over magnesium sulfate, concentrated and chromatographed eluting with 5% ethyl acetate/hexane to yield the title product: 1H NMR (300 MHz, CDCl3) δ 6.16 (d, J=3.05 Hz, 1H), 5.97 (dd, J=3.22, 0.85 Hz, 1H), 5.42 (dt, J=11.44, 7.11 Hz, 1H)), 4.14 (q, J=7.2 Hz, 2H), 2.76 (m, 2H), 2.47 (t, J=7.46 Hz, 2H), 2.31 (s, 3H), 1.25 (t, J=7.12 Hz, 3H); MS (DCI/NH3)(M+H)+ m/z 209.

1. customquenched with 2 N hydrochloric acid solution
2. extractionThe reaction mixture was extracted with ethyl acetate
3. dry with materialthe combined organic layers were dried over magnesium sulfate
4. concentrationconcentrated
5. customchromatographed
6. washeluting with 5% ethyl acetate/hexane