Hydrogen Peroxide → 2-(2-Hydroxyethyl)cyclopropylmethyl t-butyldimethylsilyl ether

HRID 36808

反応式

HRID 36808 の反応式
[Si:1]([O:8][CH2:9][CH:10]1[CH2:12][CH:11]1[CH:13]=[CH2:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-:15].[Na+].OO.[Cl-].[Na+]>O1CCCC1.C(O)C>[Si:1]([O:8][CH2:9][CH:10]1[CH2:12][CH:11]1[CH2:13][CH2:14][OH:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

参加物

7

反応物 4

HCID 784Hydrogen PeroxideHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 199379012-Vinylcyclopropylmethyl t-butyldimethylsilyl ether

生成物 1

HCID 199378982-(2-Hydroxyethyl)cyclopropylmethyl t-butyldimethylsilyl ether収率 81%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

2-vinylcyclopropylmethyl t-butyldimethylsilyl ether (17.1 g, 81 mmol) was dissolved in tetrahydrofuran (100 ml) and cooled to 0° C. A borane-dimethylsulfide complex (2.5 g, 33 mmol) was added thereto, and the mixture was stirred for one hour. Ethanol (38 ml), 3N sodium hydroxide (38 ml) and 30% hydrogen peroxide (18.2 ml) were added thereto, and the mixture was stirred for 30 minutes. The saturated sodium chloride aqueous solution was added thereto, and the product was extracted with ethyl acetate, then dried over anhydrous magnesium sulfate and concentrated. Then, it was purified by silica gel column chromatography to obtain 2-(2-hydroxyethyl)cyclopropylmethyl t-butyldimethylsilyl ether (15.0 g, yield: 81%).

後処理

  1. additionA borane-dimethylsulfide complex (2.5 g, 33 mmol) was added
  2. stirringthe mixture was stirred for 30 minutes
  3. extractionthe product was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThen, it was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-d9b5df59fa294b3fbf6ef085804eda9a
出典データセット
uspto-grants-1995_05
特許番号
US05416231

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