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

HRID 36808

Reaction equation

HRID 36808 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-d9b5df59fa294b3fbf6ef085804eda9a
Source dataset
uspto-grants-1995_05
Patent number
US05416231

Linked notes

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