Dimethylformamide → HCID 23076427, compound

HRID 2221692Notes

Reaction equation

HRID 2221692 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].[OH:21][C:22]1[CH:26]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[O:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][C:12]1[CH:13]=[CH:14][C:9]([C:5]2[O:6][C:7]([CH3:8])=[C:3]([CH2:2][O:21][C:22]3[CH:26]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[O:24][N:23]=3)[N:4]=2)=[CH:10][CH:11]=1)[CH3:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 86605723HCID 86605723, compoundHCID 178498603HCID 178498603, compound

Product 1

HCID 23076427HCID 23076427, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of ethyl [4-(4-chloromethyl-5-methyl-1,3-oxazol-2-yl)phenyl]acetate (2.00 g), methyl 3-hydroxyisoxazole-5-carboxylate (0.974 g), anhydrous potassium carbonate (0.941 g) and N,N-dimethylformamide (40 mL) was stirred at 90° C. for 2 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered through silica gel. The filtrate was concentrated to give methyl 3-({2-[4-(2-ethoxy-2-oxoethyl)phenyl]-5-methyl-1,3-oxazol-4-yl}methoxy)isoxazole-5-carboxylate as colorless crystals (2.02 g, yield 81%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 124-126° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered through silica gel
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6bbd3f52820a4bbca7c54bae53426d3a
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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