Reaktion #52854

Reaktionsgleichung

4,4-dimethyl-7-bromo-3,4-dihydronaphthalen-1(2H)one

7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1-one

Compound G

7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1-one

1-ethoxyvinyltributyltin

hydrochloric acid

EVTB

→

4,4-Dimethyl-7-acetyl-3,4-dihydronaphthalen-1(2H)-one

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   Temperaturrefluxed for an additional 24 h
3. 3
   workup.ADDITIONwas added
4. 4
   Extraktionthe mixture was extracted with ether (3×50 mL)
5. 5
   Waschenthe combined organic layer was washed with water (10 mL), 10% sodiumbicarbonate (10 mL), brine (10 mL)
6. 6
   Trocknendried with magnesium sulfate
7. 7
   SonstigeSolvent was removed under reduced pressure
8. 8
   Sonstigeafter purification by flash chromatography the title compound
9. 9
   Sonstigewas obtained as a white solid

Vorschrift

A solution of 4,4-dimethyl-7-bromo-3,4-dihydronaphthalen-1(2H)one (Compound G) (1.78 g, 7 mmol), 1-ethoxyvinyltributyltin (EVTB) (3.3 g, 9.12 mmol), bis(triphenylphosphine)palladium(II)chloride (260 mg, 0.23 mmol) in THF (25 mL) was refluxed for 24 h under argon atmosphere. To the reaction, additional EVTB (1.5 g, 4.1 mmol) and bis(triphenylphosphine)palladium(I)chloride (200 mg, 0.2 mmol) were added and the mixture was and refluxed for an additional 24 h. The reaction mixture was cooled to room temeperature and 10% hydrochloric acid (10 ml) was added. After 10 min, the mixture was extracted with ether (3×50 mL), the combined organic layer was washed with water (10 mL), 10% sodiumbicarbonate (10 mL), brine (10 mL), dried with magnesium sulfate. Solvent was removed under reduced pressure, and after purification by flash chromatography the title compound was obtained as a white solid.

Quelle