Methanol → Potassium 2-[2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetate

HRID 1294350Notes

Reaction equation

HRID 1294350 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:32]=[CH:31][C:18]([CH2:19][O:20][C:21]2[C:26]([CH2:27][C:28]([OH:30])=[O:29])=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:17][CH:16]=1.[OH-].[K+:34].CO>O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:32]=[CH:31][C:18]([CH2:19][O:20][C:21]2[C:26]([CH2:27][C:28]([O-:30])=[O:29])=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:17][CH:16]=1.[K+:34]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 99105492-[2-[4-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy)-3-pyridyl]acetic acid

Product 1

HCID 68885927Potassium 2-[2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetateYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[2-[4-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetic acid (0.20 g) was added to a mixture of a 1N aqueous potassium hydroxide solution (0.46 mL), methanol (5 mL) and tetrahydrofuran (5 mL) at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, and the residue was washed with diethyl ether to give crystals (0.19 g, yield 86%) of potassium 2-[2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetate. Recrystallization from methanol-diethyl ether gave colorless prism crystals. melting point: 157-159° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washthe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-34e8f90e96bc43fa919e8a9ff44c5862
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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