Sodium Hydroxide → HCID 87120836, compound

HRID 1470557Notes

Reaction equation

HRID 1470557 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:9]([C@@H:10]2[CH2:12][C@H:11]2[C:13]([O:15]CC)=[O:14])=[CH:8][CH:7]=[C:6]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[N:5]=1>CO>[Cl:3][C:4]1[C:9]([C@@H:10]2[CH2:12][C@H:11]2[C:13]([OH:15])=[O:14])=[CH:8][CH:7]=[C:6]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[CH:19]=2)[N:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131732726HCID 131732726, compound

Product 1

HCID 87120836HCID 87120836, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4N NaOH solution (20 mL) was added to a solution of trans-ethyl 2-(2-chloro-6-(3-(trifluoromethyl)phenyl)pyridin-3-yl)cyclopropanecarboxylate (5.5 g, 14.90 mmol), in Methanol (50 mL) and stirred at RT for 2 h. After completion, the solvent was evaporated and the residue was diluted with water (50 mL), acidified with 4 N HCl solution, extracted with EtOAc (2×50 mL). The combined extracts were washed with water (2×50 L), brine (50 mL), dried over anhydrous Na2SO4, filtered and evaporated to afford trans-2-(2-chloro-6-(3-(trifluoromethyl)phenyl)pyridin-3-yl)cyclopropanecarboxylic acid (4.9 g), as a yellow liquid. The crude was carried to next step without further purification.

Workup

  1. customAfter completion, the solvent was evaporated
  2. additionthe residue was diluted with water (50 mL)
  3. extractionextracted with EtOAc (2×50 mL)
  4. washThe combined extracts were washed with water (2×50 L), brine (50 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-ebfecca612f4490391cbb645371b9d30
Source dataset
uspto-grants-2015_04
Patent number
US09006449B2

Reaction notes

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