反应详情

温度

55 °C

To a cold solution (ice bath) of methyl phosphonoacetate (13.74 g, 0.065 mol) in tetrahydrofuran (120 mL) under nitrogen, was added sodium hydride (2.6 g, 0.065 mol, 60%) in one portion, and stirred until hydrogen evolution ceased. A solution of commercially available 5-Methoxyindole-3-carboxyaldehyde 2 (5.2 g, 0.029 mol) in tetrahydrofaran (80 mL) was added, over a period of 60 minutes, to the phosphonate solution. The reaction mixture was heated to 55° C. for 24 h after which the mixture was diluted with dichloromethane (DCM, 500 mL) and washed with water (200 mL; 3×). The organic layer was washed once with brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to give yellow-tinted oil and purified by filtering through a silica plug. The filtrate was evaporated to afford 3 as an off white solid (6.2 g; 78% yield; M+1=232.0).

1. washwashed with water (200 mL; 3×)
2. washThe organic layer was washed once with brine
3. dry with materialdried over anhydrous sodium sulfate
4. customevaporated under reduced pressure
5. customto give yellow-tinted oil
6. custompurified
7. filtrationby filtering through a silica plug
8. customThe filtrate was evaporated
9. customto afford 3 as an off white solid (6.2 g; 78% yield; M+1=232.0)