Hydrochloric Acid → (2E)-3-[6-(Trifluoromethyl)pyridin-3-yl]prop-2-enoic acid

HRID 1880611Notes

Reaction equation

HRID 1880611 reaction equation
C([O:3][C:4](=[O:17])/[CH:5]=[CH:6]/[C:7]1[CH:8]=[N:9][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:12]=1)C.[OH-].[Na+].Cl>C1COCC1.CCO>[F:15][C:13]([F:14])([F:16])[C:10]1[N:9]=[CH:8][C:7](/[CH:6]=[CH:5]/[C:4]([OH:17])=[O:3])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59526503HCID 59526503, compound

Product 1

HCID 5709645(2E)-3-[6-(Trifluoromethyl)pyridin-3-yl]prop-2-enoic acidYield 91.7%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of (E)-ethyl-3-(6-(trifluoromethyl)pyridin-3-yl)acrylate (2.65 g, 10.8 mmol) in THF/EtOH (1/1, 20 mL) was added 2.28 M NaOH (aq.) (14.2 mL) at rt. The reaction mixture was stirred at rt for 4 h and was then neutralized by adding 1M HCl(aq.). The water-phase was extracted with CH2Cl2/MeOH 9/1 (5×20 mL), the combined organics dried (MgSO4), filtered and evaporated to give the title compound (2.15 g, 9.90 mmol, 91%) as an off white solid. This material was used directly in the next step without further purification.

Workup

  1. extractionThe water-phase was extracted with CH2Cl2/MeOH 9/1 (5×20 mL)
  2. dry with materialthe combined organics dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-496c0e5c594c4f10be15ef074dae5a98
Source dataset
uspto-grants-2012_11
Patent number
US08318768B2

Reaction notes

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