Lithium Hydroxide → HCID 67086802, compound

HRID 1665170Notes

Reaction equation

HRID 1665170 reaction equation
C[O:2][C:3](=[O:20])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=1.[Li+].[OH-]>C1COCC1.CO>[N:17]1[CH:16]=[CH:15][C:14]([CH2:13][O:12][C:9]2[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:20])=[O:2])=[CH:7][CH:8]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 67087040HCID 67087040, compound

Product 1

HCID 67086802HCID 67086802, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[4-(Pyridin-4-ylmethoxy)-phenyl]-propionic acid methyl ester (0.28 g, 1.03 mmol) in THF (5 ml) and MeOH (5 ml) at room temperature is added 2 N LiOH (0.52 ml, 1.032 mmol) and the resulting solution is stirred overnight. Further 2 N LiOH (0.103 ml) is added and the reaction mixture stirred for a further 1 hour. The reaction mixture is concentrated in vacuo and the residue is diluted with water (50 ml) followed by EtOAc. The aqueous phase is acidified to pH2 with 1 N HCl, and extracted with DCM. The organic phase is concentrated to a third of its volume in vacuo until a white powder precipitates which is collected by filtration to yield the title compound; [M+H]+ 258.0

Workup

  1. stirringthe reaction mixture stirred for a further 1 hour
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. additionthe residue is diluted with water (50 ml)
  4. extractionextracted with DCM
  5. concentrationThe organic phase is concentrated to a third of its volume in vacuo until a white powder
  6. customprecipitates which
  7. filtrationis collected by filtration

Sources & evidence

ORD record
ord-33129623e8ed41009a14f3cc8e5f7812
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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