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

HRID 1294256
Notes
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Reaction equation

HRID 1294256 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.[CH2:23]([O:25][C:26]1[CH:27]=[CH:28][C:29]([OH:37])=[C:30]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH:31]=1)[CH3:24].CN(C)C=O.[H-].[Na+]>O>[CH2:23]([O:25][C:26]1[CH:27]=[CH:28][C:29]([O:37][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:30]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH:31]=1)[CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazoleHCID 17861247Methyl 2-(5-ethoxy-2-hydroxyphenyl)acetate

Product 1

HCID 68883949Methyl 2-[5-ethoxy-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetateYield 60.4%

Reagents, catalysts & solvents

1
HCID 962WaterSolvent

Procedure

To a mixture of 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (0.72 g), methyl 2-(5-ethoxy-2-hydroxyphenyl)acetate (0.40 g) and N,N-dimethylformamide (20 mL) was added sodium hydride (60%, oil, 0.08 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 methyl 2-[5-ethoxy-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetate as an oil (0.56 g, 60%) from a fraction eluted with ethyl acetate-hexane (1:4, v/v).

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-2718433334c843d08379140b048dad52
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07238716B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes