Methanol → Isoxazole, 5-methyl-4-[4-(methylsulfonyl)phenyl]-3-phenyl-

HRID 1603019Notes

Reaction equation

HRID 1603019 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=1.OOS([O-])=O.[K+].[OH2:27].C[OH:29]>>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:3]=1[C:13]1[CH:14]=[CH:15][C:16]([S:19]([CH3:20])(=[O:29])=[O:27])=[CH:17][CH:18]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962Water2×HCID 19608692HCID 19608692, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 9796841Isoxazole, 5-methyl-4-[4-(methylsulfonyl)phenyl]-3-phenyl-Yield 29%

Procedure

5-Methyl-4-[4-(methylthio)phenyl]-3-phenylisoxazole from Step 3 (100 mg, 0.355 mmol) was dissolved in methanol (20 mL). Oxone® (0.765 g, 1.24 mmol) and water (2 mL) were added, and the suspension was stirred at room temperature for 2 hours. Water was added (30 mL) and the resulting suspension was cooled to 0° C. and held for 30 minutes whereupon the product crystallized. The product was isolated by filtration, washed with water and dried to yield 5-methyl-4-[4-(methylsulfonyl)phenyl]-3-phenylisoxazole (32 mg, 29%): mp 54-56° C. Mass Spectrum: MLi+=320. High resolution mass spectrum Calc'd for C17H15NO3S: 313.077. Found: 313.078.

Workup

  1. temperaturethe resulting suspension was cooled to 0° C.
  2. waitheld for 30 minutes whereupon the product
  3. customcrystallized
  4. customThe product was isolated by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-87b53f4211f8460c9efadfaa72452084
Source dataset
uspto-grants-1999_11
Patent number
US05985902

Reaction notes

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