Tetrahydrofuran → HCID 23136688, compound

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.

1. customthe reaction liquid for 3 hours at 0° C.
2. extractionthe aqueous layer was extracted 3 times with 50 ml of ether
3. customthe organic layer was collected
4. dry with materialdried with anhydrous magnesium sulfate
5. customExcess methyltriphenylphosphonium bromide and triphenylphosphine oxide were precipitated
6. additionby adding 80 ml of n-hexane to the residues
7. customobtained by the removal of solvent
8. customAfter removing insolubles
9. filtrationby filtration
10. customthe concentrated filtrate was purified by silica gel column chromatography

ORD record

ord-4ee99baaf9a3453cb92c0f0a2980060f

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07732549B2