تفاعل #1005929

معادلة التفاعل

4-methoxy-2,3-dinitrobenzaldehyde

3,4,5-trimethoxybenzyltriphenyl phosphonium bromide

NaH

→

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

المردود 51.0%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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)

المصدر