Reacción #52854

Ecuación de reacción

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

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente