Dimethylformamide → HCID 86605868, compound

HRID 2221924Notes

Reaction equation

HRID 2221924 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:38])=[C:11]([CH2:13][O:14][C:15]3[CH:35]=[CH:34][C:18]([CH2:19][O:20][C:21]4[C:25]([CH:26]=[O:27])=[CH:24][N:23]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[N:22]=4)=[CH:17][C:16]=3[O:36][CH3:37])[N:12]=2)[CH:5]=[CH:6][CH:7]=1.Br[CH2:40][C:41]([O:43][CH3:44])=[O:42].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH:26]([C:25]1[C:21]([O:20][CH2:19][C:18]2[CH:34]=[CH:35][C:15]([O:14][CH2:13][C:11]3[N:12]=[C:8]([C:4]4[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=4)[O:1][CH2:40][C:41]([O:43][CH3:44])=[O:42])[O:9][C:10]=3[CH3:38])=[C:16]([O:36][CH3:37])[CH:17]=2)=[N:22][N:23]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:24]=1)=[O:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 86605866HCID 86605866, compound

Product 1

HCID 86605868HCID 86605868, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-[(4-{[2-(3-hydroxyphenyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazole-4-carbaldehyde (0.80 g), methyl bromoacetate (0.37 g), potassium carbonate (0.33 g) and N,N-dimethylformamide (30 mL) was stirred at 90° C. for 1 hr. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give methyl (3-{4-[(4-{[(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl}-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}phenoxy)acetate as colorless crystals (0.38 g, yield 41%) from a fraction eluted with ethyl acetate-hexane (1:2, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 107-109° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-85785c5c0ca44e2ba7ae3130d4c745da
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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