Dimethylformamide → Methyl 2-[5-bromo-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetate

HRID 1294250Notes

Reaction equation

HRID 1294250 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.[Br:23][C:24]1[CH:25]=[CH:26][C:27]([OH:35])=[C:28]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:29]=1.CN(C)C=O.[H-].[Na+]>O>[Br:23][C:24]1[CH:25]=[CH:26][C:27]([O:35][CH2:2][C:3]2[CH:22]=[CH:21][C:6]([O:7][CH2:8][C:9]3[N:10]=[C:11]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[O:12][C:13]=3[CH3:14])=[CH:5][CH:4]=2)=[C:28]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:29]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 10657986Methyl 2-(5-bromo-2-hydroxyphenyl)acetateHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazole

Product 1

HCID 68883486Methyl 2-[5-bromo-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetateYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (4.58 g), methyl 2-(5-bromo-2-hydroxyphenyl)acetate (3.0 g) and N,N-dimethylformamide (100 mL) was added sodium hydride (60%, oil, 0.54 g) under ice-cooling, and the mixture was stirred at room temperature for 15 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. After concentration of the organic layer, the residue was subjected to silica gel column chromatography to give crystals (4.46 g, 70%) of methyl 2-[5-bromo-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetate from a fraction eluted with ethyl acetate-hexane (1:6, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 100-101° C.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-28602e0caace46678ee437f974e4181c
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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