반응 #722777

반응 방정식

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

THF

hydrochloric acid

→

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

반응 조건

후처리

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

실험 절차

A solution of 4,4-dimethyl-7-bromo-3,4-dihydronaphthalen-1(2H)one (Compound G) (1.78 g, 7 mmol), 1-ethoxyyinyltributyltin (EVTB) (3.3 g, 9.12 mmol), bis(triphenylphosphine)palladium(II)chloride (260 mg, 0.23 nmol) 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(II)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.

출처