反应详情

Cinnamyl alcohol (1.52 g, 11.3 mmol) and sodium hydride (0.56 g, 14 mmol, 60% oil disp.) were stirred in dry N,N-dimethylformamide (15 mL) at room temperature under a nitrogen atmosphere for 45 minutes. After the hydrogen gas evolution had ceased, a solution of 1-benzoyl-4[(p-toluene sulfonyl)oxyethyl]piperidine (3.93 g, 11.3 mmol) in dry DMF (40 mL) was added, and the mixture was stirred for 18 hours. Additional sodium hydride (0.53 g) was added, and the reaction was further stirred for 24 hours. The reaction was quenched with saturated aqueous ammonium chloride (50 mL), and extracted with ethyl acetate (500 mL). The organic phase was extracted with water (5×50 mL), brine (50 mL), dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by chromatography on silica gel, eluting with hexanes to 50% ethyl acetate in hexanes, then concentrated under vacuum to yield (E)-1-benzoyl-4-[(3-phenyl-2-propenyloxy)ethyl]piperidine (2.55 g, 65%) as a yellow oil. IR (neat): 1630 cm-1. HRMS: Calculated for C23H27NO2 : 349.2042; found: 349.2050.

1. stirringthe reaction was further stirred for 24 hours
2. customThe reaction was quenched with saturated aqueous ammonium chloride (50 mL)
3. extractionextracted with ethyl acetate (500 mL)
4. extractionThe organic phase was extracted with water (5×50 mL), brine (50 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe crude product was purified by chromatography on silica gel
9. washeluting with hexanes to 50% ethyl acetate in hexanes
10. concentrationconcentrated under vacuum