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Dimethylformamide → Methyl 2-[3-[5-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-2-pyridylmethoxy]phenyl]acetate

HRID 1294290
Notes
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Reaction equation

HRID 1294290 reaction equation
ClC[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH2:10][C:11]2[N:12]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:14][C:15]=2[CH3:16])N=1.[OH:23][C:24]1[CH:25]=[C:26]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:27]=[CH:28][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:41][N:42](C)C=O>O>[CH3:16][C:15]1[O:14][C:13]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:12][C:11]=1[CH2:10][O:9][C:5]1[CH:6]=[CH:7][C:8]([CH2:3][O:23][C:24]2[CH:25]=[C:26]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:27]=[CH:28][CH:29]=2)=[N:42][CH:41]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 39129Methyl 3-HydroxyphenylacetateHCID 178613022-Chloromethyl-6-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine

Product 1

HCID 68883891Methyl 2-[3-[5-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-2-pyridylmethoxy]phenyl]acetateYield 87%

Reagents, catalysts & solvents

1
HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(chloromethyl)-6-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]pyridine (0.96 g), methyl 2-(3-hydroxyphenyl)acetate (0.50 g), anhydrous potassium carbonate (0.52 g) and N,N-dimethylformamide (15 mL) was stirred at 80° 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 2-[3-[5-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-2-pyridylmethoxy]phenyl]acetate as a colorless oil (1.17 g, 87%) from a fraction eluted with ethyl acetate-hexane (1:1, v/v).

Workup

  1. extractionextracted 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-44d8e6d2e1514499ada979eab4e64a76
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07238716B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes