反应 #1833207

反应方程式

4-methoxy-2,3-dinitrobenzaldehyde

3,4,5-trimethoxybenzyltriphenyl phosphonium bromide

NaH

→

2′,3′-Dinitro-3,4,4′,5-tetramethoxy-(Z)-stilbene

收率 51.0%

溶剂

dichloromethane

反应条件

后处理

1. 1
   其他The reaction was quenched
2. 2
   workup.ADDITIONby adding water
3. 3
   其他the organic layer was separated
4. 4
   萃取the aqueous layer was extracted with dichloromethane (3×25 mL)
5. 5
   洗涤The combined organic layer was washed with brine
6. 6
   干燥dried over Na2SO4
7. 7
   浓缩concentrated in vacuo to orange colored slush
8. 8
   workup.ADDITIONTo this was added about 15 mL of dichloromethane and refrigerated overnight

实验过程

4-methoxy-2,3-dinitrobenzaldehyde (2.94 mmol) and 3,4,5-trimethoxybenzyltriphenyl phosphonium bromide (1.54 g, 2.94 mmol, 1.0 equiv) in anhydrous dichloromethane (25 mL) was added NaH (0.424 g, 17.67 mmol, 6.0 equiv). The reaction mixture was stirred at room temperature for about 7 hours and monitored by TLC. The reaction was quenched by adding water, the organic layer was separated and the aqueous layer was extracted with dichloromethane (3×25 mL). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo to orange colored slush. To this was added about 15 mL of dichloromethane and refrigerated overnight. The crude mixture was subjected to flash chromatography to isolate 2′,3′-Dinitro-3,4,4′,5-tetramethoxy-(Z)-stilbene (0.581 g, 1.48 mmol, 51%, solid)

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