Reaktion #8192

Reaktionsgleichung

[2-(7-hydroxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester

bromoacetonitrile

K2CO3

→

[2-(7-cyanomethoxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester

Ausbeute 86.5%

Lösungsmittel

2-butanone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis heated to reflux
2. 2
   Temperaturto cool
3. 3
   Filtrationis filtered through celite
4. 4
   EinengenThe filtrate is concentrated to an oil which
5. 5
   Sonstigeis purified by flash chromatography with CH2Cl2

Vorschrift

A mixture of [2-(7-hydroxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester (15.55 g, 51.1 mmol), bromoacetonitrile (10.7 mL, 153 mmol), K2CO3 (17.78 g, 128.6 mmol) and 2-butanone is heated to reflux. After 1 hour the mixture is allowed to cool and is filtered through celite. The filtrate is concentrated to an oil which is purified by flash chromatography with CH2Cl2 followed by 5% ethyl acetate/CH2Cl2 to give 15.18 g of [2-(7-cyanomethoxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester (86%). MS (ES−) m/z 342.

Quelle