Dimethylformamide → 2-[5-Methoxymethoxy-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetonitrile

HRID 1294107Notes

Reaction equation

HRID 1294107 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][C:27]([O:30][CH2:31][O:32][CH3:33])=[CH:26][C:25]=1[CH2:34][C:35]#[N:36].CN(C)C=O.[H-].[Na+]>O>[CH3:33][O:32][CH2:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][CH2:2][C:3]2[CH:22]=[CH:21][C:6]([O:7][CH2:8][C:9]3[N:10]=[C:11]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[O:12][C:13]=3[CH3:14])=[CH:5][CH:4]=2)=[C:25]([CH2:34][C:35]#[N:36])[CH:26]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazoleHCID 178612602-(2-Hydroxy-5-methoxymethoxyphenyl)acetonitrile

Product 1

HCID 688858772-[5-Methoxymethoxy-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetonitrileYield 57.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (1.95 g), 2-(2-hydroxy-5-methoxymethoxyphenyl)acetonitrile (1.0 g) and N,N-dimethylformamide (50 mL) was added sodium hydride (60%, oil, 0.23 g) under ice-cooling, and the mixture was stirred at 80° C. for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The organic, layer was washed successively with water, 2N aqueous sodium hydroxide solution and 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 crystals (1.40 g, 57%) of 2-[5-methoxymethoxy-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetonitrile from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 123-124° C.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic, layer was washed successively with water, 2N aqueous sodium hydroxide solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-49a337df5680471788a66f42b4085c5e
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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