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Hydrogen Peroxide → HCID 54508019, compound

HRID 1197039
Notes
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Reaction equation

HRID 1197039 reaction equation
[OH:1][CH:2]([CH:12]1[C:16](=[O:17])[CH:15]=[CH:14][CH:13]1[CH:18]=[CH:19][CH:20]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9].[OH:34]O.[OH-].[Na+]>CO>[O:34]1[CH:14]2[CH:15]1[C:16](=[O:17])[CH:12]([CH:2]([OH:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])[CH:13]2[CH:18]=[CH:19][CH:20]([O:26][Si:27]([C:30]([CH3:32])([CH3:31])[CH3:33])([CH3:29])[CH3:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 571788985-(1-Hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone

Product 1

HCID 54508019HCID 54508019, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3.30 g of 5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone in methanol (25 ml) was cooled to 0° C., and 48 ml of an aqueous 30% hydrogen peroxide and 0.48 ml of an aqueous 1N sodium hydroxide were dropwise added thereto. After stirring at 0° C. for 3 hours, the reaction mixture was extracted with an addition of ethyl acetate and saturated aqueous ammonium chloride, and the extract was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered, followed by concentration. The concentrate was subjected to silica gel chromatography to give 2.54 g (yield 74%) of 2,3-epoxy-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)cyclopentanone.

Workup

  1. extractionthe reaction mixture was extracted with an addition of ethyl acetate and saturated aqueous ammonium chloride
  2. washthe extract was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-032269fd74b04e04a8dfc4dfbee765c8
Source dataset
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05116869

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes