反应详情

A suspension of methyl triphenylphosphonium bromide (2.41 g, 6.74 mmol) in THF (20 ml) was added dropwise potassium tert-butoxide (756 mg, 6.74 mmol) in THF (20 ml) at 0° C., and the mixture was stirred at room temperature for 1.5 hours. Then, methyl 6-acetyl-2-naphthoate (J. Org. Chem., 1990, 55, 319-324, 769 mg, 3.37 mmol) in THF (5 ml) was added at room temperature, and the resulting mixture was stirred at room temperature for 2 hours. The reaction was quenched with water (100 ml) and extracted with ethyl acetate-hexane (1:2). The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude material was purified by silica gel column chromatography, eluting with ethyl acetate-hexane (0:100 to 1:20) to give 0.67 g (88% yield) of the title compound as white solid. 1H NMR (270 MHz, CDCl3) δ 2.28 (3H, s), 3.99 (3H, s), 5.26 (1H, s), 5.58 (1H, s), 7.74 (1H, d, J=8.6 Hz), 7.82-7.97 (3H, m), 8.05 (1H, d, J=8.6 Hz), 8.58 (1H, s).

1. stirringthe resulting mixture was stirred at room temperature for 2 hours
2. customThe reaction was quenched with water (100 ml)
3. extractionextracted with ethyl acetate-hexane (1:2)
4. dry with materialThe organic layer was dried over sodium sulfate
5. concentrationconcentrated in vacuo
6. customThe crude material was purified by silica gel column chromatography
7. washeluting with ethyl acetate-hexane (0:100 to 1:20)