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Hydrogen Peroxide → HCID 54508019、化合物

HRID 1197039
ノート
印刷プレビュー

反応式

HRID 1197039 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

HCID 54508019HCID 54508019、化合物収率 74%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-032269fd74b04e04a8dfc4dfbee765c8
出典データセット
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05116869

反応ノート

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