反応 #1005929

反応方程式

4-methoxy-2,3-dinitrobenzaldehyde

3,4,5-trimethoxybenzyltriphenyl phosphonium bromide

NaH

→

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

収率 51.0%

溶媒

dichloromethane

反応条件

後処理

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

実験手順

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)

出典