Triethylamine → HCID 66744940, compound

Temperature

0 °C

Potassium 3-(ethoxy)-3-oxopropanoate (6.06 g, 35.6 mmol) was suspended in acetonitrile (100 mL), cooled to 0° C. and treated successively with triethylamine (4.96 mL, 35.6 mmol, 1 equiv) and anhydrous magnesium(II) chloride (3.39 g, 35.6 mmol, 1 equiv). The ice bath was removed and the mixture was warmed to ambient temperature and stirred for 2.5 hours. An acetonitrile (5 mL) solution of 2-fluoropyridine-3-carbonyl choride (5.68 g, 35.6 mmol) was added and the mixture was stirred for 72 hours at ambient temperature. The mixture was concentrated in vacuo and the residue was concentrated from toluene (1×75 mL). The residue was suspended in toluene (50 mL), cooled to 0° C. and treated with hydrochloric acid (20 mL, 12 N aqueous). After 15 minutes, the mixture was warmed to ambient temperature and stirred for an additional 45 minutes. The mixture was poured into water (50 mL) and extracted with ethyl acetate (3×75 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 1:1; hexanes:ethyl acetate), providing the titled compound.

1. customThe ice bath was removed
2. temperaturethe mixture was warmed to ambient temperature
3. stirringthe mixture was stirred for 72 hours at ambient temperature
4. concentrationThe mixture was concentrated in vacuo
5. concentrationthe residue was concentrated from toluene (1×75 mL)
6. temperaturecooled to 0° C.
7. additiontreated with hydrochloric acid (20 mL, 12 N aqueous)
8. waitAfter 15 minutes
9. temperaturethe mixture was warmed to ambient temperature
10. stirringstirred for an additional 45 minutes
11. additionThe mixture was poured into water (50 mL)
12. extractionextracted with ethyl acetate (3×75 mL)
13. dry with materialThe combined organic extracts were dried with sodium sulfate
14. filtrationfiltered
15. concentrationconcentrated in vacuo
16. customThe residue was purified by silica gel gradient chromatography (100:0 to 1:1; hexanes:ethyl acetate)

ORD record

ord-a9f77296b9a8433c89666f02a2764396

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08293744B2