Methanol → HCID 54565608, compound

HRID 266509Notes

Reaction equation

HRID 266509 reaction equation
Br[CH:2]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][C:12]=1[Cl:21])[C:3]1[CH:4]=[N:5][O:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1.[CH3:22][OH:23]>C1(C)C=CC=CC=1>[CH3:22][O:23][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][C:12]=1[Cl:21])[C:3]1[CH:4]=[N:5][O:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 887MethanolHCID 18924611HCID 18924611, compound

Product 1

HCID 54565608HCID 54565608, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-[bromo-(2-chloro-4-methanesulphonylphenyl)-methyl]-5-cyclopropylisoxazole (2.5 g) and methanol (2.0 ml) in toluene was stirred at reflux for 16 hours. The resultant solution was evaporated to dryness and the residue was dissolved in ethyl acetate. This solution was washed with water, dried (MgSO4), and filtered. The filtrate was evaporated to dryness. The residue was purified by chromatography on silica eluted with ethyl acetate and petroleum ether to give 4-[methoxy-(2-chloro-4-methanesulphonyl-phenyl)methyl]-5-cyclopropylisoxazole (compound 307, 1.40 g) as a colourless oil, NMR: (CDCl3) 1.0(4H, m), 2.1 (1H, m), 3.0(3H,s), 3.3(3H, s), 5.6(1H,s), 7.9(4H,m).

Workup

  1. temperatureat reflux for 16 hours
  2. customThe resultant solution was evaporated to dryness
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThis solution was washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customThe residue was purified by chromatography on silica
  9. washeluted with ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-18663e0cddaa43dfbc294db17d283248
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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