Reaktion #65086

Reaktionsgleichung

sodium chloride

sodium hydroxide

hydrogen peroxide

2-vinylcyclopropylmethyl t-butyldimethylsilyl ether

→

2-(2-hydroxyethyl)cyclopropylmethyl t-butyldimethylsilyl ether

Ausbeute 81.0%

Lösungsmittel

Ethanol

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA borane-dimethylsulfide complex (2.5 g, 33 mmol) was added
2. 2
   workup.STIRRINGthe mixture was stirred for 30 minutes
3. 3
   Extraktionthe product was extracted with ethyl acetate
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Einengenconcentrated
6. 6
   SonstigeThen, it was purified by silica gel column chromatography

Vorschrift

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%).

Quelle