Reaktion #803633

Reaktionsgleichung

7-(4-tert-butylphenyl)-2-methyl-1H-indene

nBuLi

chloro[6-isopropyl-2-methyl-5-(pentafluorophenoxy)-4-phenyl-1H-inden-1-yl]dimethylsilane

CuCN

→

title product

Ausbeute 53.0%

[4-(4-tert-Butylphenyl)-2-methyl-1H-inden-1-yl][6-isopropyl-2-methyl-5-(pentafluoro phenoxy)-4-phenyl-1H-inden-1-yl]dimethylsilane

Ausbeute 53.0%

Lösungsmittel

water

—

hexanes

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to −40° C.
2. 2
   workup.STIRRINGThe resulting mixture was stirred for 1 h at −20° C.
3. 3
   Temperaturcooled to −40° C.
4. 4
   workup.STIRRINGFurther on, this mixture was stirred overnight at ambient temperature
5. 5
   FiltrationThis solution was filtered through a pad of silica gel 60 (40-63 um) which
6. 6
   Waschenwas then additionally washed by 2×75 ml of dichloromethane
7. 7
   WaschenThe combined organic elute
8. 8
   Sonstigewas evaporated to dryness
9. 9
   Sonstigethe residue was dried in vacuum
10. 10
    SonstigeThe product was isolated by flash-chromatography on silica gel 60 (40-63 um

Vorschrift

To a solution of 6.39 g (24.4 mmol) of 7-(4-tert-butylphenyl)-2-methyl-1H-indene in 200 ml of ether 9.80 ml (24.5 mmol) of 2.5 M nBuLi in hexanes was added in one portion at −40° C. This mixture was stirred overnight at room temperature, then cooled to −40° C., and 150 mg of CuCN was added. The resulting mixture was stirred for 1 h at −20° C., then cooled to −40° C., and a solution of 10.5 g (20.0 mmol) of chloro[6-isopropyl-2-methyl-5-(pentafluorophenoxy)-4-phenyl-1H-inden-1-yl]dimethylsilane in 200 ml of ether was added in one portion. Further on, this mixture was stirred overnight at ambient temperature, then 0.5 ml of water was added. This solution was filtered through a pad of silica gel 60 (40-63 um) which was then additionally washed by 2×75 ml of dichloromethane. The combined organic elute was evaporated to dryness, and the residue was dried in vacuum. The product was isolated by flash-chromatography on silica gel 60 (40-63 um; eluent: hexanes-dichloromethane=10:1, vol., then 5:1, vol.). This procedure gave 7.86 g (53%) of the title product (of ca. 90% purity as a ca. 1:1 mixture of the stereoisomers on the evidence of NMR spectroscopy) as a yellowish glass.

Quelle