반응 #44141

반응 방정식

2-(methoxy)-1-[(E)-2-(methoxy)ethenyl]-3-nitrobenzene

2-(methyloxy)-1-[(Z)-2-(methyloxy)ethenyl]-3-nitrobenzene

2-(methoxy)-3-nitrobenzaldehyde

18-Crown-6

(methoxymethyl)triphenylphosphonium chloride

potassium carbonate

sodium carbonate

→

title compound

수율 54.0%

[2-(Methoxy)-3-nitrophenyl]acetaldehyde

수율 54.0%

용매

hydrochloric acid

THF

THF

반응 조건

후처리

1. 1
   온도then cooled to room temperature
2. 2
   여과filtered
3. 3
   농축The filtrate was concentrated under vacuum
4. 4
   기타purified by chromatography on a silica cartridge (eluent cyclohexane-ethyl acetate, 9:1)
5. 5
   기타to give
6. 6
   추출extracted with DCM
7. 7
   세척The organic layer was washed (water, brine)
8. 8
   건조dried (sodium sulfate)
9. 9
   농축concentrated under vacuum

실험 절차

To a stirred solution of 2-(methoxy)-3-nitrobenzaldehyde in THF were added 18-Crown-6 (0.2 eq), (methoxymethyl)triphenylphosphonium chloride (2 eq) and potassium carbonate (6.5 eq). The resulting suspension was warmed to 60° C. for 2 hours then cooled to room temperature and filtered. The filtrate was concentrated under vacuum and purified by chromatography on a silica cartridge (eluent cyclohexane-ethyl acetate, 9:1) to give a mixture of 2-(methoxy)-1-[(E)-2-(methoxy)ethenyl]-3-nitrobenzene and 2-(methyloxy)-1-[(Z)-2-(methyloxy)ethenyl]-3-nitrobenzene. The alkene mixture was dissolved in THF and 6N hydrochloric acid (1:1), and stirred for 1 hour. The solution was made basic with aqueous sodium carbonate solution and extracted with DCM. The organic layer was washed (water, brine), dried (sodium sulfate) and concentrated under vacuum to give the title compound (54% overall yield).

출처