Reaktion #803627

Reaktionsgleichung

water

(6-tert-butyl-5-methoxy-2-methyl-4-phenyl-1H-inden-1-yl)(chloro)dimethylsilane

5-tert-butyl-2-methyl-7-phenyl-1H-indene

nBuLi

→

yellowish glassy solid

Ausbeute 72.4%

(6-tert-Butyl-5-methoxy-2-methyl-4-phenyl-1H-inden-1-yl)-(6-tert-butyl-2-methyl-4-phenyl-1H-inden-1-yl)dimethylsilane

Ausbeute 72.4%

Lösungsmittel

ether

ether

—

hexanes

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to −78° C.
2. 2
   workup.STIRRINGThe resulting mixture was stirred for 30 min at −20° C.
3. 3
   Temperaturcooled to −78° C.
4. 4
   workup.STIRRINGThis mixture was stirred overnight at room temperature
5. 5
   Sonstigethe elute was evaporated to dryness
6. 6
   SonstigeThe product was isolated by flash-chromatography on silica gel 60 (40-63 um

Vorschrift

To a solution of 14.5 g (55.4 mmol) of 5-tert-butyl-2-methyl-7-phenyl-1H-indene in 400 ml of ether cooled to −78° C., 22.2 ml (55.5 mmol) of 2.5 M nBuLi in hexanes was added. This mixture was stirred overnight at room temperature, then cooled to −78° C., and 200 mg (2.23 mmol) of CuCN was added. The resulting mixture was stirred for 30 min at −20° C., then cooled to −78° C., and a solution of 21.2 g (55.4 mmol) of (6-tert-butyl-5-methoxy-2-methyl-4-phenyl-1H-inden-1-yl)(chloro)dimethylsilane in 200 ml of ether was added. This mixture was stirred overnight at room temperature, then 1 ml of water was added. The obtained mixture was passed through a short layer of silica gel 60 (40-63 um), the elute was evaporated to dryness. The product was isolated by flash-chromatography on silica gel 60 (40-63 um; eluent: hexanes-dichloromethane=10:1, vol., then 3:1, vol.). This procedure gave 24.5 g (72%) of yellowish glassy solid.

Quelle