Reacción #1005929

Ecuación de reacción

4-methoxy-2,3-dinitrobenzaldehyde

3,4,5-trimethoxybenzyltriphenyl phosphonium bromide

NaH

→

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

Rendimiento 51.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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)

Fuente