反応 #11247
ord-5d80c8c706d54d52b27d08212a2f23ba
反応方程式
試薬
反応条件
後処理
- 1温度The reaction mixture was cooled to room temperature
- 2その他the tetrahydrofuran was removed
- 3workup.ADDITIONWater (50 mL) was added
- 4抽出the mixture was extracted with ethyl acetate (3×100 mL)
- 5洗浄The combined ethyl acetate extracts were washed with brine (50 mL)
- 6乾燥dried over magnesium sulphate
- 7ろ過filtered
- 8濃縮concentrated to dryness
- 9その他Trituration with diethyl ether (20 mL) gave solid material which
- 10洗浄was further washed with diethyl ether (20 ml)
- 11濃縮The liquors were concentrated
- 12その他triturated with diethyl ether (10 mL)
- 13その他the solid being collected
実験手順
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.