m-Chloroperbenzoic acid → HCID 86746912, compound

HRID 1587136Notes

Reaction equation

HRID 1587136 reaction equation
[CH3:1][S:2]([C:4]1[C:5](=[O:29])[C:6](=[CH:20]/[CH:21]=[CH:22]\[CH:23]([OH:28])[CH2:24][CH2:25][CH2:26][OH:27])[C:7](=[CH:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=1)=[O:3].ClC1C=CC=C(C(OO)=[O:38])C=1.C(=O)([O-])O.[Na+]>ClCCl>[CH3:1][S:2]([C:4]1[C:5](=[O:29])[C:6](=[CH:20]/[CH:21]=[CH:22]\[CH:23]([OH:28])[CH2:24][CH2:25][CH2:26][OH:27])[C:7](=[CH:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:8]=1)(=[O:38])=[O:3]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86746913HCID 86746913, compound

Product 1

HCID 86746912HCID 86746912, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6.5 mg of 2-methylsulfinyl-5-[(Z)-4,7-dihydroxy-2-heptenylidene]-4-(4-phenoxybutylidene)-2-cyclopentenone obtained in Example 573 or Example 574 dissolved in 1.5 ml of dichloromethane was added 3 mg of 3-chloroperbenzoic acid, and the mixture was stirred for 4 hours. Saturated aqueous sodium hydrogencarbonate was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated, followed by silica gel chromatography to give 3.9 mg (yield 60%) of 2-methylsulfonyl-5-[(Z)-4,7-dihydroxy-2-heptenylidene]-4-(4-phenoxybutylidene)-2-cyclopentenone.

Workup

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

Sources & evidence

ORD record
ord-55f8600ecb7b4277b5dbc6d19042442e
Source dataset
uspto-grants-1993_06
Patent number
US05216183

Reaction notes

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