反应详情

To a suspension of hexane-washed sodium hydride (0.14 g of 60% suspension in mineral oil, 3.45 mmol) in 20 mL of THF was added trimethyl phosphonoacetate (0.56 mL, 3.45 mmol). The resulting mixture was stirred for 30 min at ambient temperature, at which time a white slurry was obtained. To this slurry was added ethyl 2-chloro-6-formyl-4-propylbenzoate (0.80 g, 3.14 mmol) dropwise in 5 mL of THF. The resulting solution was stirred at ambient temperature for 1 h, at which time the mixture had become homogeneous. The reaction mixture was quenched with water and extracted with ethyl acetate. The organics were washed sequentially with 1N HCl, sat'd aq NaHCO3 and brine, dried (MgSO4), filtered through a pad of silica gel and concentrated in vacuo to afford 0.92 g (95%) of the title compound which was sufficiently pure to be used without purification. 1H NMR (CDCl3): δ 7.58 (d, 1H, J=15.9 Hz), 7.25 (s, 1H), 7.18 (s, 1H), 6.33 (d, 1H, J=15.9 Hz), 4.40 (q, 2H, J=7.2 Hz), 3.73 (s, 3H), 2.52 (t, 2H, J=7.5 Hz), 1.60-1.52 (m, 2H), 1.35 (t, 3H, J=7.1 Hz), 0.88 (t, 3H, J=7.4 Hz). LRMS (ESI): 333.1 (M+H+Na)+.

1. customwas obtained
2. stirringThe resulting solution was stirred at ambient temperature for 1 h, at which time the mixture
3. customThe reaction mixture was quenched with water
4. extractionextracted with ethyl acetate
5. washThe organics were washed sequentially with 1N HCl
6. dry with materialdried (MgSO4)
7. filtrationfiltered through a pad of silica gel
8. concentrationconcentrated in vacuo