Hydrogen Peroxide → HCID 54508019, compound

HRID 1197039Notes

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]

Participants

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

extractionthe reaction mixture was extracted with an addition of ethyl acetate and saturated aqueous ammonium chloride
washthe extract was washed with saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
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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