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

HRID 1294349Notes

Reaction equation

HRID 1294349 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.O.[OH-].[Li+:35].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.[Li+:35]

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 99105492-[2-[4-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy)-3-pyridyl]acetic acid

Product 1

HCID 68886310Lithium 2-[2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl)acetateYield 91.1%

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 lithium hydroxide monohydrate (19 mg), methanol (5 mL) and tetrahydrofuran (5 mL) at room temperature, and the mixture was stirred for 30 min. The reaction mixture was concentrated, and the residue was crystallized from methanol and diethyl ether to give crystals (0.18 g, yield 90%) of lithium 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: 207-209° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was crystallized from methanol and diethyl ether

Sources & evidence

ORD record
ord-172dcf780344445fb7913d3039307295
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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