Ethyl Acetate → HCID 59594672, compound

HRID 2263418Notes

Reaction equation

HRID 2263418 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl[CH2:12][C:13]1[O:17][C:16]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[N:15][C:14]=1[CH3:30].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:12][C:13]2[O:17][C:16]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:22][CH:21]=3)=[N:15][C:14]=2[CH3:30])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 5927972-Chloro-4-hydroxybenzonitrileHCID 595948035-Chloromethyl-4-methyl-2-[2-(4-trifluoromethyl-phenyl)-ethyl]-oxazole

Product 1

HCID 59594672HCID 59594672, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.63 g 2-chloro-4-hydroxy-benzonitrile in 25 ml dimethylformamide were added 4.0 g 5-chloromethyl-4-methyl-2-[2-(4-trifluoromethyl-phenyl)-ethyl]-oxazole and 8.58 g cesium carbonate. The mixture was stirred at room temperature overnight. Then 150 ml of ethyl acetate were added, the mixture washed with 40 ml water and brine and then dried over MgSO4. The solvent was removed in vacuo. The resulting crude material was purified by RP-HPLC to obtain 3.0 g 2-chloro-4-{4-methyl-2-[2-(4-trifluoromethyl-phenyl)-ethyl]-oxazol-5-ylmethoxy}-benzonitrile.

Workup

  1. washthe mixture washed with 40 ml water and brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed in vacuo
  4. customThe resulting crude material was purified by RP-HPLC

Sources & evidence

ORD record
ord-727c348f7a13411aa627974a7db2a8ad
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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