반응 #1005929

반응 방정식

4-methoxy-2,3-dinitrobenzaldehyde

3,4,5-trimethoxybenzyltriphenyl phosphonium bromide

NaH

→

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

수율 51.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   기타The reaction was quenched
2. 2
   workup.ADDITIONby adding water
3. 3
   기타the organic layer was separated
4. 4
   추출the aqueous layer was extracted with dichloromethane (3×25 mL)
5. 5
   세척The combined organic layer was washed with brine
6. 6
   건조dried over Na2SO4
7. 7
   농축concentrated in vacuo to orange colored slush
8. 8
   workup.ADDITIONTo this was added about 15 mL of dichloromethane and refrigerated overnight

실험 절차

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)

출처