Potassium Acetate → HCID 20230276, compound

HRID 2290779Notes

Reaction equation

HRID 2290779 reaction equation
Cl[CH2:2][C:3]1[N:7]=[C:6]([CH:8]([CH3:22])[C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([F:21])[CH:10]=2)[O:5][N:4]=1.[C:23]([O-:26])(=[O:25])[CH3:24].[K+]>CN(C=O)C.O>[C:23]([O:26][CH2:2][C:3]1[N:7]=[C:6]([CH:8]([CH3:22])[C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([F:21])[CH:10]=2)[O:5][N:4]=1)(=[O:25])[CH3:24]

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 136909413-Chloromethyl-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazole

Product 1

HCID 20230276HCID 20230276, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.32 g of 3-chloromethyl-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole in 30 ml of dry DMF was added 1.58 g of potassium acetate. After stirring at room temperature overnight, the reaction mixture was diluted with water and extracted with benzene. The organic phase was washed with water, dried over sodium sulfate and evaporated. The residue was chromatographed over silica gel using benzene to yield 0.96 g of 3-acetoxymethyl-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole, nD23 1.5635.

Workup

  1. extractionextracted with benzene
  2. washThe organic phase was washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-df9ec027b36f430381ffdd920b4712ba
Source dataset
uspto-grants-1986_10
Patent number
US04618617

Reaction notes

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