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

HRID 36808

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HRID 36808 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-d9b5df59fa294b3fbf6ef085804eda9a
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05416231

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