反应详情

A 10 mL Schenk tube was dried in oven and loaded under N2 with K3PO4 (2.37 g, 11.16 mmol) and DMA (2.0 mL). 3-iodobenzaldeide (1.85 g, 7.97 mmol) and n-butylacrylate. (2.28 mL, 15.94 mmol) were then added by syringe. A solution of Pd(OAc)2 (0.18 g, 0.797 mmol) in DMA (0.5 mL) was further added by syringe. The Schlenk tube was then sealed under nitrogen and placed in a pre-heated oil bath at 140° C., and the reaction mixture was stirred for 24 h. After cooling to room temperature, the reaction mixture was poured in water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with brine, dried (Na2SO4), and concentrated under vacuum to dryness. The crude product was purified by chromatographic column on silica gel, eluting with n-hexane/ethylacetate/methanol 12/3/1 (yield: 47%). 1H NMR (CDCl3) δ: 0.91-0.96 (t, 3H, OCH2CH2CH2CH3), 1.39-1.42 (m, 2H, OCH2CH2CH2CH3), 1.65-1.68 (m, 2H, OCH2CH2CH2CH3), 4.17-4.21 (m, 2H, OCH2CH2CH2CH3), 6.48-6.53 (d, 1H, ArCH═CHCO), 7.52-7.54 (m, 1H, benzene H-5), 7.53-7.75 (m, 2H, ArCH═CHCO and benzene H-6), 7.84-7.86 (m, 1H, benzene H-4), 7.99 (m, 1H, benzene H-2), 10.01 (s, 1H, CHO).

1. customA 10 mL Schenk tube was dried in oven
2. addition(2.28 mL, 15.94 mmol) were then added by syringe
3. customThe Schlenk tube was then sealed under nitrogen
4. customplaced in a pre-heated oil bath at 140° C.
5. extractionextracted with ethyl acetate (3×50 mL)
6. washThe combined organic extracts were washed with brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated under vacuum to dryness
9. customThe crude product was purified by chromatographic column on silica gel