Reacción #50166

Ecuación de reacción

tetrahydrofuran

butyllithium

bromide

THF

methyl 4-formylbenzoate

→

methyl 4-(2-methoxyethenyl)benzoate

Disolventes

hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added to a solution
2. 2
   workup.ADDITIONwas added
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITwas continued for two hours
5. 5
   LavadoThe reaction solution was washed with water
6. 6
   Secadodried over magnesium sulfate
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   OtroThe residue was purified by column chromatography

Procedimiento

In an atmosphere of argon, a solution containing butyllithium dissolved in hexane was added to a solution containing 120 g of methoxymethyltriphenylphosphoni bromide dissolved in tetrahydrofuran (THF), and the mixture was stirred for one hour at room temperature. A solution containing 50 g of methyl 4-formylbenzoate dissolved in THF was added thereto, and stirring was continued for two hours. The reaction solution was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to obtain 47 g of methyl 4-(2-methoxyethenyl)benzoate (45).

Fuente