Ethanol → Ethyl 5-chloronicotinate

Temperatur

50 °C

To ethanol (66 mL) and DMF (66 mL) was added Et3N (29.4 mL), 1,3-propanediylbis(diphenylphosphine) (3.48 g) and palladium acetate (1.9 g) in ice-water bath. To this was added 5-chloro-3-pyridinyl trifluoromethanesulfonate (22.1 g) at the temperature. The mixture was stirred at 50° C. for 4 hours under CO (1 atom). The mixture was partitioned betwwen EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layer was washed with water three times, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel column chromatography (silica gel, 200 mL) eluted with hexane-EtOAc=15-1 and 10-1 to give ethyl 5-chloronicotinate (10.5 g) as a pale brown oil.

1. customThe mixture was partitioned betwwen EtOAc and water
2. extractionThe aqueous layer was extracted with EtOAc
3. washThe combined organic layer was washed with water three times
4. dry with materialdried over MgSO4
5. customevaporated in vacuo
6. customThe residue was purified by silica gel column chromatography (silica gel, 200 mL)
7. washeluted with hexane-EtOAc=15-1 and 10-1

ORD-Eintrag

ord-dafd1bc7eebc408db612b16b6ca81d4f

Quelldatensatz

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07153854B2