2,2,2-Trifluoroethanol → 183368-79-8

HRID 341562Notes

Reaction equation

HRID 341562 reaction equation
F[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.CC(C)([O-])C.[K+].[F:17][C:18]([F:22])([F:21])[CH2:19][OH:20]>O.Cl>[F:17][C:18]([F:22])([F:21])[CH2:19][O:20][C:2]1[N:3]=[CH:4][CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9]

Participants

6

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 960892-Fluoronicotinic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 15267492183368-79-8Yield 32%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

2-Fluoropyridine-3-carboxylic acid (200 mg, 1.42 mmol) was dissolved in 2,2,2-trifluoroethanol (2 mL) and potassium tert-butoxide (477 mg, 4.25 mmol) was added. The mixture was then heated to 90 C for 4 h. The mixture was diluted with water (4 mL), 2M HCl was added to bring the solution to pH 4 and the mixture was extracted with DCM (3×4 mL). 2M HCl was added to the aqueous layer to bring the solution to pH 3 and the mixture was extracted with DCM (4×5 mL). The combined organic extractions were dried over sodium sulfate and evaporated under vacuum to afford the title compound (100 mg, 32%). Method C HPLC-MS: MH+ requires m/z=222. Found: m/z=222, Rt=1.17 min (100%).

Workup

  1. temperatureThe mixture was then heated to 90 C for 4 h
  2. additionwas added
  3. extractionthe mixture was extracted with DCM (3×4 mL)
  4. addition2M HCl was added to the aqueous layer
  5. extractionthe mixture was extracted with DCM (4×5 mL)
  6. extractionThe combined organic extractions
  7. dry with materialwere dried over sodium sulfate
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-5254a25280c74f60bc8c56bb6b9715b8
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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