Reaktion #65087

Reaktionsgleichung

sodium hydrogen carbonate

triphenylphosphine

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

Bromine

→

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

Ausbeute 14.2%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat room temperature
2. 2
   Temperaturthe temperature was gradually raised to 0° C
3. 3
   Extraktionthe product was extracted with ethyl ether
4. 4
   TrocknenThen, it was dried over anhydrous magnesium sulfate
5. 5
   Sonstigepurified by silica gel column chromatography

Vorschrift

2-(2-hydroxyethyl)cyclopropylmethyl t-butyldimethylsilyl ether (15.0 g, 65 mmol) was dissolved in N,N-dimethylformamide (120 ml), and triphenylphosphine (17.3 g, 66 mmol) was added thereto at room temperature. Twenty minutes later, the mixture was cooled to -20° C. Bromine (10.5 g, 66 mmol) was added thereto over a period of 5 minutes, and the temperature was gradually raised to 0° C. The mixture was poured into a saturated sodium hydrogen carbonate aqueous solution, and the product was extracted with ethyl ether. Then, it was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain 2-(2-bromoethyl)cyclopropylmethyl t-butyldimethylsilyl ether (2.7 g).

Quelle