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

HRID 611027Notes

Reaction equation

HRID 611027 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

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 temperature 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.

Workup

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

Sources & evidence

ORD record
ord-87026cd1989643c8864caf6f01408879
Source dataset
uspto-grants-1999_12
Patent number
US05998655

Reaction notes

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