Water → HCID 22221489, compound

HRID 1794427Notes

Reaction equation

HRID 1794427 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[CH2:14][CH2:15][CH2:16][OH:17])=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:26])C=1.O>C(#N)C>[CH3:1][S:2]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[CH2:14][CH2:15][CH2:16][OH:17])=[CH:7][CH:8]=1)=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 69561763HCID 69561763, compound

Product 1

HCID 22221489HCID 22221489, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-[5-(4-methylthiophenyl)-4-isoxazolyl]propan-1-ol (900 mg) in acetonitrile (20 ml) was gradually added m-chloroperbenzoic acid (750 mg) at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into iced water and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and crystals (390 mg, yield 41%) of 3-[5-(4-methylsulfinylphenyl)-4-isoxazolyl]propan-1-ol were obtained from a fraction eluted with acetone-hexane (2:1, volume ratio). The crystals were recrystallized from ethyl acetate-diethyl ether to give a colorless prism. melting point: 73–74° C.

Workup

  1. customat 0° C.
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bf75a8cbc1bd4c8e80ea61da22a53b3a
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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