Reaktion #576005

Reaktionsgleichung

2,6-dimethoxy-phenylboronic acid

6-bromo-1,1,4,4 tetramethy 1,2,3,4-tetrahydronaphthalene

potassium carbonate

→

6-(2,6-Dimethoxyphenyl)-1,1,4,4-tetramethy-1,2,3,4-tetrahydronaphthlene

Ausbeute 103.5%

Lösungsmittel

ethyl acetate

1,2-dimethoxyethane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas degassed with argon for 15 minutes
2. 2
   Temperaturthe mixture heated
3. 3
   Temperaturat reflux under argon for 5 hours
4. 4
   Waschenwashed successively with water and brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe residue was chromatographed on silica gel (eluent: ethyl acetate/hexane, 1:9)

Vorschrift

A mixture of 2,6-dimethoxy-phenylboronic acid (1.0 g, 5.48 mmol), 6-bromo-1,1,4,4 tetramethy 1,2,3,4-tetrahydronaphthalene (0.73 g, 2.74 mmol) and potassium carbonate (1.50 g, 10.96 mmol) in 1,2-dimethoxyethane (20 mL) and water (1.0 mL) was degassed with argon for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.60 g, 0.54 mmol) was added and the mixture heated at reflux under argon for 5 hours. The solution was cooled to room temperature, diluted with ethyl acetate and washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was chromatographed on silica gel (eluent: ethyl acetate/hexane, 1:9) to give 0.92 g of 6-(2,6-Dimethoxyphenyl)-1,1,4,4-tetramethy-1,2,3,4-tetrahydronaphthlene.

Quelle