Methoxymethyl-triphenylphosphonium chloride → HCID 86670916, compound

To a suspension of (methoxymethyl)triphenylphosphonium chloride (34.5 g, 100.6 mmol) in THF (500 mL) at −10° C. was added LDA (60 mL, 2 mol/L). The mixture was stirred at −10° C. for 1 hour before addition of 6-bromopicolinaldehyde (10 g, 53.8 mmol) in THF (200 mL). The reaction mixture was then allowed to warm to room temperature and stirred at room temperature for 12 hours. The solution was then partitioned between water and ether. The aqueous fraction was separated and extracted twice with ether. The organic layers were washed with brine and dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to give the crude product which was purified by chromatography (petroleum ether:ethyl acetate, 20:1) to give 2-bromo-6-(-2-methoxy-vinyl)-pyridine. (Yield 9.3 g, 80%). LC-MS: [M+H]+ 215.

1. customThe solution was then partitioned between water and ether
2. customThe aqueous fraction was separated
3. extractionextracted twice with ether
4. washThe organic layers were washed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationThe filtrate was concentrated under reduced pressure
8. customto give the crude product which
9. customwas purified by chromatography (petroleum ether:ethyl acetate, 20:1)

ORD record

ord-082173651f9645d897543c1fa6150f80

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673905B2