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

HRID 1294301Notes

Reaction equation

HRID 1294301 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][OH:22])[CH:18]=[N:19][CH:20]=1.S(Cl)(Cl)=O.O[C:28]1[CH:33]=[CH:32][C:31]([CH2:34][C:35]([O:37][CH3:38])=[O:36])=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>O.CN(C)C=O.C1(C)C=CC=CC=1.O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][O:22][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][C:35]([O:37][CH3:38])=[O:36])=[CH:30][CH:29]=2)[CH:18]=[N:19][CH:20]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 178612255-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethanol

Product 1

HCID 68886274Methyl 2-[4-[5-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-3-pyridylmethoxy]phenyl)acetateYield 84.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [5-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-3-pyridyl]methanol (1.20 g), thionyl chloride (0.6 mL), tetrahydrofuran (20 mL) and toluene (20 mL) was stirred at room temperature for 2 hrs. The precipitated crystals were collected by filtration and washed with diisopropyl ether to give crude crystals. A mixture of the obtained crystals, methyl 2-(4-hydroxyphenyl)acetate (0.70 g), anhydrous potassium carbonate (0.92 g) and N,N-dimethylformamide (20 mL) was stirred overnight at 80° C. 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-[4-[5-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-3-pyridylmethoxy]phenyl]acetate as a pale-yellow oil (1.52 g, 0.84%) from a fraction eluted with ethyl acetate-hexane (1:1, v/v).

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. washwashed with diisopropyl ether
  3. customto give crude crystals
  4. stirringwas stirred overnight at 80° C
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-26da33f8cc374f2a86d81181f9ef5c50
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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