反应 #44141

反应方程式

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

收率 54.0%

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

收率 54.0%

溶剂

hydrochloric acid

THF

THF

反应条件

后处理

1. 1
   温度then cooled to room temperature
2. 2
   过滤filtered
3. 3
   浓缩The filtrate was concentrated under vacuum
4. 4
   其他purified by chromatography on a silica cartridge (eluent cyclohexane-ethyl acetate, 9:1)
5. 5
   其他to give
6. 6
   萃取extracted with DCM
7. 7
   洗涤The organic layer was washed (water, brine)
8. 8
   干燥dried (sodium sulfate)
9. 9
   浓缩concentrated under vacuum

实验过程

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).

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