تفاعل #1079300

معادلة التفاعل

EVTB

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

→

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

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwere added
2. 2
   درجة الحرارةrefluxed for an additional 24 h
3. 3
   workup.ADDITIONwas added
4. 4
   استخلاصthe mixture was extracted with ether (3×50 mL)
5. 5
   غسيلthe combined organic layer was washed with water (10 mL), 10% sodiumbicarbonate (10 mL), brine (10 mL)
6. 6
   تجفيفdried with magnesium sulfate
7. 7
   أخرىSolvent was removed under reduced pressure
8. 8
   أخرىafter purification by flash chromatography the title compound
9. 9
   أخرىwas obtained as a white solid

الإجراء التجريبي

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(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.

المصدر