반응 #43529

반응 방정식

potassium tertiary butoxide

potassium tertiary butoxide

THF

3,5-bis(methoxymethyl)benzaldehyde

THF

→

3,5-bis(methoxymethyl)styrene

수율 67.0%

용매

water

반응 조건

후처리

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

실험 절차

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.

출처