Tetrahydrofuran → (4-Pyridin-2-YL-phenyl)-acetic acid

HRID 1362784Notes

Reaction equation

HRID 1362784 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([O:16]C)=[O:15])=[CH:9][CH:8]=1.O1CCCC1.[OH-].[K+]>O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 12094242Methyl 2-(4-(pyridin-2-yl)phenyl)acetate

Product 1

HCID 504301(4-Pyridin-2-YL-phenyl)-acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

700 mg (3.11 mol) of methyl [4-(2-pyridyl)phenyl]acetate are introduced into 5 ml of tetrahydrofuran and, at room temperature, 6.2 ml of a 1M potassium hydroxide solution in water are added. The mixture is stirred at room temperature for 18 h and then the solvent is substantially removed in vacuo, the residue is taken up in 10 ml of water and the pH was adjusted to about 5 with 2N hydrochloric acid. Extraction of the aqueous phase twice with 10 ml of dichloromethane each time affords, after drying the combined organic phases over magnesiumsulfate and removing the solvent in vacuo, the compound of Example VIII in the form of a solid.

Workup

  1. customthe solvent is substantially removed in vacuo
  2. extractionExtraction of the aqueous phase twice with 10 ml of dichloromethane each time
  3. customaffords
  4. dry with materialafter drying the combined organic phases over magnesiumsulfate
  5. customremoving the solvent in vacuo

Sources & evidence

ORD record
ord-f304a59ac13b458e9d7ba4b592e74e36
Source dataset
uspto-grants-2011_02
Patent number
US07883713B2

Reaction notes

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