Water → HCID 22221077, compound

HRID 1794426Notes

Reaction equation

HRID 1794426 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.[OH2:29]>O1CCCC1>[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])=[O:29]

Participants

5

Reactant 3

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

Product 1

HCID 22221077HCID 22221077, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[5-(4-methylthiophenyl)-4-isoxazolyl]propan-1-ol (500 mg) in tetrahydrofuran (30 ml) was gradually added m-chloroperbenzoic acid (870 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 to give crystals (480 mg, yield 85%) of 3-[5-(4-methylsulfonylphenyl)-4-isoxazolyl]propan-1-ol from a fraction eluted with acetone-hexane (1:1, volume ratio). The crystals were recrystallized from ethyl acetate-isopropyl ether to give a colorless needle. melting point: 125–126° 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-5be720a15fee45c882dfadd3d09df25c
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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