Dimethylformamide → HCID 68884954, compound

HRID 1294111Notes

Reaction equation

HRID 1294111 reaction equation
Cl[CH2:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:12][C:13]=2[CH3:14])=[CH:5][CH:4]=1.[OH:23][C:24]1[CH:25]=[C:26]([C:30]([O:32][CH3:33])=[O:31])[CH:27]=[N:28][CH:29]=1.CN(C)C=O.[H-].[Na+]>O>[CH3:14][C:13]1[O:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:10][C:9]=1[CH2:8][O:7][C:6]1[CH:21]=[CH:22][C:3]([CH2:2][O:23][C:24]2[CH:25]=[C:26]([C:30]([O:32][CH3:33])=[O:31])[CH:27]=[N:28][CH:29]=2)=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 354317Methyl 5-hydroxypyridine-3-carboxylateHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazole

Product 1

HCID 68884954HCID 68884954, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (4.52 g), methyl 5-hydroxy-3-pyridinecarboxylate (2.0 g), and N,N-dimethylformamide (30 mL) was added sodium hydride (60%, oil, 0.58 g) under ice-cooling, and the mixture was stirred at room temperature for 3 hrs. The reaction mixture was poured into water, and the precipitated crystals were collected by filtration. The crystals were subjected to silica gel column chromatography to give crystals (2.41 g, 0.43%) of methyl 5-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridinecarboxylate from a fraction eluted with ethyl acetate-hexane (1:1, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 138-139° C.

Workup

  1. temperaturecooling
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-89aa8ead91354bebb1d6b8ae8eb947a1
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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