Sodium Thiosulfate → HCID 86745878, compound

HRID 1587140Notes

Reaction equation

HRID 1587140 reaction equation
[OH:1][CH:2]([CH2:27][CH2:28][CH2:29][OH:30])/[CH:3]=[CH:4]/[CH:5]=[C:6]1[C:10](=[O:11])[C:9]([S:12]([CH3:14])=[O:13])=[CH:8][C:7]1([OH:26])[CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.ClC1C=CC=C(C(OO)=[O:39])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[OH:1][CH:2]([CH2:27][CH2:28][CH2:29][OH:30])/[CH:3]=[CH:4]/[CH:5]=[C:6]1[C:10](=[O:11])[C:9]([S:12]([CH3:14])(=[O:39])=[O:13])=[CH:8][C:7]1([OH:26])[CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 86745877HCID 86745877, compound

Product 1

HCID 86745878HCID 86745878, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 165 mg of 5-[(E)-4,7-dihydroxyheptenylidene]-4-hydroxy-2-methylsulfinyl-4-(4-phenoxybutyl)-2-cyclopentenone obtained in Example 582 dissolved in 30 ml of dichloromethane was added a solution 117 mg of 3-chloroperbenzoic acid in 5 ml of dichloromethane, and the mixture was stirred for 2 hours. The reaction mixture was poured onto saturated aqueous sodium thiosulfate, and the mixture was extracted 3 times with ethyl acetate. The organic layers were combined, washed twice with saturated aqueous sodium hydrogencarbonate and with saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. After filtration and concentration, the concentrate was subjected to chromatography to give 78 mg (yield 47%) of 5-[(E)-4,7-dihydroxy-2-heptenylidene]-4-hydroxy-2-methylsulfonyl-4-(4-phenoxybutyl)-2-cyclopentenone.

Workup

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. washwashed twice with saturated aqueous sodium hydrogencarbonate and with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-68fa76a6d1d54e43b4c1ad5657945efd
Source dataset
uspto-grants-1993_06
Patent number
US05216183

Reaction notes

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