反应详情

A solution of O,O-diethyl 3-trifluoromethylbenzylphosphonate (20.0 g, 67.5 mmol) in tetrahydrofuran (90 mL) was cooled to -70° C. (dry ice bath), under N2, and a solution of butyllithium (1.6M, in hexanes, 46.4 mL, 74.3 mmol) in 90 mL of dry tetrahydrofuran cooled to -70° C. (dry ice) was added. After 15 minutes, a solution of 3-trifluoromethylbenzylbromide (10.3 mL, 67.5 mmol)in tetrahydrofuran (90 mL) was added. The green reaction mixture turned yellow and was brought to room temperature and allowed to stir for 4 hours. The mixture was then quenched with H2O (200 mL), and extracted with ether (2×200 mL). The combined ether extracts were dried (MgSO4), filtered, and concentrated to dryness to give a yellow oil, 32.3 g. The crude product was chromatographed on a silica gel column. Elution with ethyl acetate/hexane (1:1) afforded analytically pure product as a pale yellow oil, 24.1 g (78.4 %). 300 MHz 1H NMR (CDCl3): δ, 3.16-4.20 (m,7H, PCH, PhCH2, 2(OCH2). MS: 455 (M+1).

1. additionwas added
2. customwas brought to room temperature
3. customThe mixture was then quenched with H2O (200 mL)
4. extractionextracted with ether (2×200 mL)
5. dry with materialThe combined ether extracts were dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated to dryness
8. customto give a yellow oil, 32.3 g
9. customThe crude product was chromatographed on a silica gel column
10. washElution with ethyl acetate/hexane (1:1)
11. customafforded analytically pure product as a pale yellow oil, 24.1 g (78.4 %)