반응 #11543

반응 방정식

Potassium carbonate

N,N-Dimethylformamide

4-acetylpyridine

(benzyloxycarbonyl)methyltriphenylphosphonium bromide

→

benzyl 3-(4-pyridyl)-2-butenoate

수율 42.4%

용매

diethyl ether

반응 조건

후처리

1. 1
   온도cooling
2. 2
   workup.STIRRINGthe whole was stirred overnight
3. 3
   세척the whole was washed with water (100 ml
4. 4
   건조The organic layer was dried over magnesium sulfate
5. 5
   농축concentrated under reduced pressure
6. 6
   기타The residue was purified by silica gel column chromatography

실험 절차

N,N-Dimethylformamide (33 ml) was added to a mixture of 4-acetylpyridine (2.00 g, 16.5 mmol) and (benzyloxycarbonyl)methyltriphenylphosphonium bromide (8.94 g, 18.2 mmol), and the whole was stirred under ice-cooling. Potassium carbonate (9.12 g, 66.0 mmol) was added thereto, the external temperature was raised to 70° C., and the whole was stirred overnight. The reaction mixture was diluted with diethyl ether (100 ml), and the whole was washed with water (100 ml, twice) and saturated brine (50 ml) successively. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 1.77 g (42%: mixture of E form and Z form) of benzyl 3-(4-pyridyl)-2-butenoate as a pale yellow oily matter.

출처