m-Chloroperbenzoic acid → HCID 54470789, compound

HRID 1197057Notes

Reaction equation

HRID 1197057 reaction equation
[OH:1][CH:2]([CH:11]1[C:15](=[O:16])[C:14]([S:17][CH3:18])=[CH:13][C:12]1([OH:30])[CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:3]=[CH:4][CH:5]([OH:10])[CH2:6][CH2:7][CH2:8][OH:9].ClC1C=CC=C(C(OO)=[O:39])C=1.C(=O)([O-])O.[Na+]>ClCCl>[OH:1][CH:2]([CH:11]1[C:15](=[O:16])[C:14]([S:17]([CH3:18])=[O:39])=[CH:13][C:12]1([OH:30])[CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH:3]=[CH:4][CH:5]([OH:10])[CH2:6][CH2:7][CH2:8][OH:9]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 53756288HCID 53756288, compound

Product 1

HCID 54470789HCID 54470789, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 35 mg of 5-(1,4,7-trihydroxy-2-heptenyl)-4-hydroxy-2-methylthio-4-(4-phenoxybutyl)-2-cyclopentenone obtained in Example 72 dissolved in 2 ml of dichloromethane was added 16 mg of 3-chloroperbenzoic acid, and the mixture was stirred for 3 hours. Saturated aqueous sodium hydrogencarbonate was added, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated, followed by silica gel column chromatography to give 7.3 mg (yield 46%) of 5-(1,4,7-trihydroxy-2-heptenyl)-4-hydroxy-2-methylsulfinyl-4-(4-phenoxybutyl)-2-cyclopentenone.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-74c90a7e3b7e4823a14960a21cca8b91
Source dataset
uspto-grants-1992_05
Patent number
US05116869

Reaction notes

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