Cesium carbonate → HCID 59594740, compound

HRID 2263423Notes

Reaction equation

HRID 2263423 reaction equation
Cl[CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1.[Cl:24][C:25]1[CH:32]=[C:31]([OH:33])[CH:30]=[CH:29][C:26]=1[C:27]#[N:28].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[Cl:24][C:25]1[CH:32]=[C:31]([O:33][CH2:2][C:3]2[O:7][C:6]([C:8]3[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=3)=[N:5][C:4]=2[CH2:16][O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH:30]=[CH:29][C:26]=1[C:27]#[N:28]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 5927972-Chloro-4-hydroxybenzonitrileHCID 59296137HCID 59296137, compound

Product 1

HCID 59594740HCID 59594740, compoundYield 118.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.5 g 5-Chloromethyl-2-(4-methoxy-phenyl)-4-(tetrahydro-pyran-2-yloxymethyl)-oxazole and 1.48 g 2-chloro-4-hydroxybenzonitrile were dissolved in 20 ml dimethylformamide. 4.82 g Cesium carbonate were added and the reaction mixture stirred at room temperature overnight. The reaction mixture was diluted with 200 ml ethyl acetate and washed five times with portions of 50 ml water and brine. The organic phase was dried over MgSO4 and the solvent was evaporated in vacuo to obtain 4.0 g crude 2-chloro-4-[2-(4-methoxy-phenyl)-4-(tetrahydro-pyran-2-yloxymethyl)-oxazol-5-ylmethoxy]-benzonitrile. This material was used without further purification.

Workup

  1. washwashed five times with portions of 50 ml water and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-f0e2e8d543654a7b9dd74f199647e0c8
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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