Dimethylformamide → HCID 68884261, compound

HRID 1294145Notes

Reaction equation

HRID 1294145 reaction equation
[C:1]([C:9]1[CH:36]=[CH:35][C:12]([O:13][CH2:14][C:15]2[CH:34]=[CH:33][C:18]([O:19][CH2:20][C:21]3[N:22]=[C:23]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[O:24][C:25]=3[CH3:26])=[CH:17][CH:16]=2)=[CH:11][C:10]=1[OH:37])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[H-].[Na+].Br[CH2:46][C:47]([O:49][CH3:50])=[O:48]>O>[C:1]([C:9]1[CH:36]=[CH:35][C:12]([O:13][CH2:14][C:15]2[CH:34]=[CH:33][C:18]([O:19][CH2:20][C:21]3[N:22]=[C:23]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[O:24][C:25]=3[CH3:26])=[CH:17][CH:16]=2)=[CH:11][C:10]=1[O:37][CH2:46][C:47]([O:49][CH3:50])=[O:48])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 17861229HCID 17861229, compound

Product 1

HCID 68884261HCID 68884261, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-[4-(4-benzoyl-3-hydroxyphenoxymethyl)phenoxymethyl]-5-methyl-2-phenyloxazole (1.52 g) and N,N-dimethylformamide (20 mL) was added sodium hydride (60%, oil, 0.14 g) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. Methyl bromoacetate (0.57 g) was added to the mixture and the mixture was stirred at 80° C. for 2 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-[2-benzoyl-5-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenoxy]acetate as an oil (1.65 g, 94%) from a fraction eluted with ethyl acetate-hexane (1:2, v/v).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 80° C. for 2 hrs
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-ff97cda04f354910ac32ae48db148e60
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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