Lithium Hydroxide → 2-Pyridinecarboxylicacid,5-(2,2,3,3-tetrafluoropropoxy)-

HRID 571747Notes

Reaction equation

HRID 571747 reaction equation
[OH-].[Li+].[F:3][C:4]([F:20])([CH:17]([F:19])[F:18])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]([O:15]C)=[O:14])=[N:11][CH:12]=1>C1COCC1.O>[F:20][C:4]([F:3])([CH:17]([F:19])[F:18])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]([OH:15])=[O:14])=[N:11][CH:12]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 574758745-(2,2,3,3-Tetrafluoro-propoxy)-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 574758552-Pyridinecarboxylicacid,5-(2,2,3,3-tetrafluoropropoxy)-Yield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Lithium hydroxide (469 mg, 19.6 mmol) is added to a solution of methyl 5-(2,2,3,3-tetrafluoropropoxy)pyridine-2-carboxylate (1.047 mg, 3.92 mmol) in THF (7 mL) and water (7 mL). The reaction mixture is stirred for 1 hour at 60° C., cooled to ambient temperature, quenched with 1 M HCl (20 mL), diluted with brine and extracted with dichloromethane (3 times). The organic layers are combined, dried over MgSO4, filtered, and concentrated under reduced pressure to give the title compound (921 mg, 93%). ES/MS (m/e): 254.0 (M+1).

Workup

  1. temperaturecooled to ambient temperature
  2. customquenched with 1 M HCl (20 mL)
  3. additiondiluted with brine
  4. extractionextracted with dichloromethane (3 times)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-71bf07925f1542c8b3527966e4d90b39
Source dataset
uspto-grants-2015_05
Patent number
US09029367B2

Reaction notes

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