Reacción #43529

Ecuación de reacción

potassium tertiary butoxide

potassium tertiary butoxide

THF

3,5-bis(methoxymethyl)benzaldehyde

THF

→

3,5-bis(methoxymethyl)styrene

Rendimiento 67.0%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction liquid for 3 hours at 0° C.
2. 2
   Extracciónthe aqueous layer was extracted 3 times with 50 ml of ether
3. 3
   Otrothe organic layer was collected
4. 4
   Secadodried with anhydrous magnesium sulfate
5. 5
   OtroExcess methyltriphenylphosphonium bromide and triphenylphosphine oxide were precipitated
6. 6
   workup.ADDITIONby adding 80 ml of n-hexane to the residues
7. 7
   Otroobtained by the removal of solvent
8. 8
   OtroAfter removing insolubles
9. 9
   Filtraciónby filtration
10. 10
    Otrothe concentrated filtrate was purified by silica gel column chromatography

Procedimiento

Then 30 ml of THF solution containing 8.36 g (43.0 mmol) 3,5-bis(methoxymethyl)benzaldehyde was added dropwise into 40 ml of THF solution containing 18.5 g (51.7 mmol) of methyltriphenylphosphonium bromide and 7.24 g (64.5 mmol) of potassium tertiary butoxide at 0° C. After agitating the reaction liquid for 3 hours at 0° C., 30 ml of water was added to deactivate the remaining potassium tertiary butoxide. The organic layer was aliquoted and the aqueous layer was extracted 3 times with 50 ml of ether and the organic layer was collected and dried with anhydrous magnesium sulfate. Excess methyltriphenylphosphonium bromide and triphenylphosphine oxide were precipitated by adding 80 ml of n-hexane to the residues obtained by the removal of solvent. After removing insolubles by filtration, the concentrated filtrate was purified by silica gel column chromatography to obtain 5.52 g (28.7 mmol) of the target 3,5-bis(methoxymethyl)styrene as a colorless oily matter.

Fuente