Reaction #2994

Reaction equation

sodium chloride

3-nitro-4-methylbenzaldehyde

3,4,5-trimethoxybenzyltriphenylphosphine bromide

sodium hydride

→

intended compound

Yield 49.6%

(Z)-1-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)ethene

Yield 49.6%

Solvents

benzene

benzene

acetic acid

Conditions

Workup

1. 1
   workup.ADDITIONdispersed
2. 2
   workup.ADDITIONtherein was added
3. 3
   Otherreacted for 15 hours at room temperature
4. 4
   OtherThe reaction liquid
5. 5
   workup.ADDITIONwas added
6. 6
   Extractionthe resulting liquid was extracted with dichloromethane
7. 7
   DryingThe extract was dried with anhydrous sodium sulfate
8. 8
   Concentrationconcentrated
9. 9
   Otherpurified by silica gel column chromatography (diethyl ether:hexane=1:2 by volume)

Procedure

1.0 g of 3-nitro-4-methylbenzaldehyde and 3.3 g of 3,4,5-trimethoxybenzyltriphenylphosphine bromide were dissolved in 50 ml of benzene, and a benzene solution containing 302 mg of sodium hydride dispersed therein was added thereto and reacted for 15 hours at room temperature. The reaction liquid was neutralized with acetic acid, saturated sodium chloride solution was added thereto, and the resulting liquid was extracted with dichloromethane. The extract was dried with anhydrous sodium sulfate, concentrated and then purified by silica gel column chromatography (diethyl ether:hexane=1:2 by volume) to obtain 0.99 g of the intended compound. The yield of the product was 47.8%.

Source