Hexane → HCID 23260319, compound

Temperature

-78 °C

A stirred suspension of methoxymethyltriphenyl phosphonium chloride (12.48 g) in tetrahydrofuran (60 ml) under argon was cooled in an ice-bath. Potassium tert-butoxide (36.41 ml, 1M solution in tetrahydrofuran) was then added dropwise over 30 minutes to give a deep orange-red colour. Stirring was continued at 0-5° C. for 50 minutes then the mixture was cooled to −78° C. 2-Pyridinecarboxaldehyde was added dropwise and stirring continued at −78° C. for a further 2 h then allowed to warm to room temperature and stirred for 2 h. Hexane (100 ml) was added, the mixture filtered and the filtrate evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting, with 10% ethyl acetate in hexane to give the pure cis-2-(2-methoxyvinyl)pyridine (0.91 g, 24%):

1. temperaturewas cooled in an ice-bath
2. customto give a deep orange-red colour
3. stirringstirring
4. waitcontinued at −78° C. for a further 2 h
5. temperatureto warm to room temperature
6. stirringstirred for 2 h
7. filtrationthe mixture filtered
8. customthe filtrate evaporated in vacuo
9. customThe residue was purified by column chromatography on silica gel eluting, with 10% ethyl acetate in hexane

ORD record

ord-aa953c5308734f00ade5a25e0cec211a

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07358376B2