Water → HCID 21914453, compound

HRID 1245778Notes

Reaction equation

HRID 1245778 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.Cl[CH2:13][C:14]1[C:15]([CH3:20])=[N:16][O:17][C:18]=1[CH3:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:20][C:15]1[C:14]([CH2:13][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:6][CH:7]=2)=[C:18]([CH3:19])[O:17][N:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 88246Isoxazole, 4-(chloromethyl)-3,5-dimethyl-HCID 70192744-Hydroxyphenylacetone

Product 1

HCID 21914453HCID 21914453, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-hydroxyphenyl acetone (1.5 g), 4-chloromethyl-3,5-dimethylisoxazole (1.6 g) and potassium carbonate (1.5 g) in dimethylformamide (10 ml) was heated and stirred at 60° C. for 18 h. After cooling, the mixture was poured into water and extracted twice with ethyl acetate. The combined solvent phase was washed twice with brine, dried (magnesium sulphate) and then evaporated. The resultant oil was chromatographed on silica using isohexane to 20% ethyl acetate in isohexane mixtures to give the title compound (2.5 g).

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling
  3. extractionextracted twice with ethyl acetate
  4. washThe combined solvent phase was washed twice with brine
  5. dry with materialdried (magnesium sulphate)
  6. customevaporated
  7. customThe resultant oil was chromatographed on silica

Sources & evidence

ORD record
ord-7aa332d8291546cfb6a8293e979d3a09
Source dataset
uspto-grants-2006_10
Patent number
US07125896B2

Reaction notes

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