Hydrochloric Acid → 3,4-dihydro-4,4-dimethyl-7-acetyl-1(2H)-naphthalenone

HRID 481212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 481212
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:14])([CH3:13])[CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[CH2:15]([O:17]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:16].Cl>C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:13][C:6]1([CH3:14])[C:5]2[C:10](=[CH:11][C:2]([C:15](=[O:17])[CH3:16])=[CH:3][CH:4]=2)[C:9](=[O:12])[CH2:8][CH2:7]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 619414Stannane, tributyl(1-ethoxyethenyl)-2×HCID 107533577-Bromo-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-one2×

Produkt 1

HCID 223237263,4-dihydro-4,4-dimethyl-7-acetyl-1(2H)-naphthalenone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysator2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. additionwere added
  2. temperaturerefluxed for an additional 24 h
  3. additionwas added
  4. extractionthe mixture was extracted with ether (3×50 mL)
  5. washthe combined organic layer was washed with water (10 mL), 10% sodiumbicarbonate (10 mL), brine (10 mL)
  6. dry with materialdried with magnesium sulfate
  7. customSolvent was removed under reduced pressure
  8. customafter purification by flash chromatography the title compound
  9. customwas obtained as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-6812435d30cd4838b2c4c1516a32432f
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06653483B1

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