반응 #11247
ord-5d80c8c706d54d52b27d08212a2f23ba
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시약
반응 조건
후처리
- 1온도The reaction mixture was cooled to room temperature
- 2기타the tetrahydrofuran was removed
- 3workup.ADDITIONWater (50 mL) was added
- 4추출the mixture was extracted with ethyl acetate (3×100 mL)
- 5세척The combined ethyl acetate extracts were washed with brine (50 mL)
- 6건조dried over magnesium sulphate
- 7여과filtered
- 8농축concentrated to dryness
- 9기타Trituration with diethyl ether (20 mL) gave solid material which
- 10세척was further washed with diethyl ether (20 ml)
- 11농축The liquors were concentrated
- 12기타triturated with diethyl ether (10 mL)
- 13기타the solid being collected
실험 절차
To a solution of diethyl 2-chlorobenzylphosphonate (4.91 g, 0.018 mol) and 7-bromo-5-methoxybenzofuran-2-carbaldehyde (11.27 g, 0.016 mol) in tetrahydrofuran (80 mL) was added sodium hydride (60% dispersion in mineral oil, 0.74 g, 0.0185 mol). After 5 min. the reaction mixture was warmed to 60° C. for 1 h. The reaction mixture was cooled to room temperature, water (10 mL) was carefully added and the tetrahydrofuran was removed. Water (50 mL) was added and the mixture was extracted with ethyl acetate (3×100 mL). The combined ethyl acetate extracts were washed with brine (50 mL), dried over magnesium sulphate, filtered and concentrated to dryness. Trituration with diethyl ether (20 mL) gave solid material which was further washed with diethyl ether (20 ml). The liquors were concentrated and triturated with diethyl ether (10 mL), the solid being collected. The combined solids gave (859) (4.89 g, 84%). 1H NMR δ (CDCl3) 7.70 (d, J=16 Hz, 1H), 7.65 (dd, J=7.7, 1.5 Hz, 1H), 7.4 (dd, J=6.0, 1 Hz, 1H), 7.23 (m, 2H), 7.05 (d, J=2.3 Hz, 1H), 6.94 (d, J=16 Hz, 1H), 6.92 (d, J=2.3 Hz, 1H), 6.72 (s, 1H), 3.82 (s, 3H); MH+:364.9, 362.9 MH−:362.9, 360.9.