Tetrahydrofuran → HCID 53949575, compound

HRID 343083Notes

Reaction equation

HRID 343083 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10](SC)=[CH:9][CH:8]=2)=[C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:4][N:3]=1.O[O:22][S:23]([O-:25])=O.[K+].O1CCC[CH2:28]1>CO.O>[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([S:23]([CH3:28])(=[O:25])=[O:22])=[CH:9][CH:8]=2)=[C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:4][N:3]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 54423472HCID 54423472, compound

Product 1

HCID 53949575HCID 53949575, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-methyl-4-(4-methylthiophenyl)-5-phenylisoxazole (Step 3) (285 mg, 1 mmol) in tetrahydrofuran and methanol (1:1) was added a solution of Oxone® (900 mg, 1.5 mmol) in water (5 ml). The reaction mixture was stirred rapidly at 25° C. for 3 hours. The reaction mixture was extracted with ethyl acetate and the organic extracts dried. After filtration and solvent removal, the crude residue was recrystallized from ethyl acetate and hexane to give pure product as a crystalline solid (250 mg, 79%): mp 144°-145° C. Anal. Calc'd. for C17H15NO3S (313.38): C, 65.16; H, 4.82; N, 4.47; S, 10.23. Found: C, 65.26; H, 4.78; N, 3.99; S, 10.22.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. customthe organic extracts dried
  3. filtrationAfter filtration and solvent removal
  4. customthe crude residue was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-8ce3466ce14b43ad938d6ba9dca810b0
Source dataset
uspto-grants-1999_01
Patent number
US05859257

Reaction notes

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