Dimethylformamide → HCID 68883766, compound

HRID 1294243Notes

Reaction equation

HRID 1294243 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:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>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:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2794569Methyl 3-(2-hydroxyphenyl)propionateHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazole

Product 1

HCID 68883766HCID 68883766, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (0.60 g), methyl 3-(2-hydroxyphenyl)propionate (0.345 g), anhydrous potassium carbonate (0.529 g) and N,N-dimethylformamide (7 mL) was stirred at room temperature for 18 hrs., and further at 70° C. for 5 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography to give methyl 3-[2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]propionate as an oil (0.61 g, 70%) from a fraction eluted with ethyl acetate-hexane (1:3, v/v).

Workup

  1. wait, and further at 70° C. for 5 hrs
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-09274d84e77648e1b4f785108e7d92cb
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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