Methoxymethyl-triphenylphosphonium chloride → HCID 54361418, compound

Temperature

0 °C

A suspension of 29.0 g of methoxymethyl-triphenylphosphonium chloride in 200 ml of t-butyl methyl ether in a sulphonation flask fitted with a mechanical stirrer is treated while gassing with argon at -10° C. within 3 minutes with 9.7 g of potassium t-butylate. The orange suspension is stirred at about 0° C. for a further 1 hour, then treated dropwise at -10° C. within 10 minutes with a solution of 14.76 g of 2-(p-bromophenyl)-5-pyridinecarboxaldehyde in 90 ml of t-butyl methyl ether and stirred at 0° C. for a further 45 minutes. The reaction mixture is subsequently partitioned three times in diethyl ether/water. The organic extracts are washed twice with water, dried over magnesium sulphate, filtered and evaporated. In order to separate triphenylphosphine oxide, the residue is dissolved in ethyl acetate and the solution is diluted with petroleum ether, filtered and evaporated. Purification of the residue by chromatography on silica gel gives 2-(p-bromophenyl)-5-(2-methoxyvinyl)pyridine.

1. customfitted with a mechanical stirrer
2. additionis treated
3. stirringstirred at 0° C. for a further 45 minutes
4. customThe reaction mixture is subsequently partitioned three times in diethyl ether/water
5. washThe organic extracts are washed twice with water
6. dry with materialdried over magnesium sulphate
7. filtrationfiltered
8. customevaporated
9. customIn order to separate triphenylphosphine oxide
10. dissolutionthe residue is dissolved in ethyl acetate
11. additionthe solution is diluted with petroleum ether
12. filtrationfiltered
13. customevaporated
14. customPurification of the residue by chromatography on silica gel

ORD record

ord-b2e5d49c03a944e3b08263308b2829fa

Source dataset

uspto-grants-1990_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04898455