Dichloromethane → (6-Ethenylpyridin-3-yl)methanol

Temperature

80 °C

A 100 mL sealed tube was charged with a solution of (6-chloropyridin-3-yl)methanol (0.5 g, 3.4 mmol, Org. Lett. 2005, p 2965-2967) dissolved in isopropanol (10 mL), potassium vinyltrifluoroborate (1 g, 7.63 mmol, Aldrich), [1,1,-bis(diphenyl phosphino)ferrocine]dichloro palladium(II) complex with DCM (0.277 g, 0.34 mmol, Aldrich) and TEA (0.92 mL, 6.8 mmol). The mixture was degassed with nitrogen then heated at about 80° C. for about 12 h. The reaction mixture was cooled to RT, filtered and washed with isopropanol (10 mL). The filtrate was evaporated to dryness under reduced pressure and the crude material obtained was purified by silica gel column chromatography using 30 to 40% of EtOAc in hexane as an eluent. Relevant fractions containing the target compound were combined and evaporated to dryness under reduced pressure to afford (6-vinylpyridin-3-yl)methanol as a dark brown liquid 0.25 g (53%), 1H NMR (400 MHz, DMSO): δ 8.479 (s, 1H), 7.704-7.688 (d, J=6.4 Hz, 1H), 7.471-7.456 (d, J=6.0 Hz, 1H), 6.827-6.806 (m, 1H), 6.212-6.177 (d, J=14 Hz, 1H), 5.439-5.417 (d, J=8.8 Hz, 1H), 5.300 (m, 1H), 4.524 (d, J=4.4 Hz, 2H), MS m/z: 136 (M+H)+.

1. customA 100 mL sealed tube
2. customThe mixture was degassed with nitrogen
3. temperatureThe reaction mixture was cooled to RT
4. filtrationfiltered
5. washwashed with isopropanol (10 mL)
6. customThe filtrate was evaporated to dryness under reduced pressure
7. customthe crude material obtained
8. customwas purified by silica gel column chromatography
9. additionRelevant fractions containing the target compound
10. customevaporated to dryness under reduced pressure

ORD record

ord-b83d4182065441678738f8cee5d7f3df

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09029409B2