Water → HCID 21914453, compound

HRID 2421300Notes

Reaction equation

HRID 2421300 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-f8237436648d45d1b5fd5adcbc32113b
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

Loading…