Stannane, tributyl(1-ethoxyethenyl)- → HCID 22491033, compound

HRID 2180560Notes

Reaction equation

HRID 2180560 reaction equation
C([Sn](CCCC)(CCCC)C(OCC)=C)CCC.[CH2:19]([O:21][C:22]1[C:23]([C:37](=[O:39])[CH3:38])=[CH:24][C:25]2[C:26](C(C)C)=[CH:27][CH2:28][C:29]([CH3:33])([CH3:32])[C:30]=2[CH:31]=1)[CH3:20]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:19]([O:21][C:22]1[C:23]([C:37](=[O:39])[CH3:38])=[CH:24][C:25]2[CH:26]=[CH:27][CH2:28][C:29]([CH3:32])([CH3:33])[C:30]=2[CH:31]=1)[CH3:20]

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-2×HCID 22491007HCID 22491007, compound

Product 1

HCID 22491033HCID 22491033, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of mixture B (2.18 g, 7.21 mmol) in THF (40 mL) was added tributyl(1-ethoxyvinyl)tin (3.66 mL, 10.8 mmol). After the mixture was degassed via bubbling argon for 30 min, dichlorobis(triphenylphosphine)palladium (II) (0.25 g, 0.05 mmol) was added. The reaction mixture was heated to reflux for 48 h. Because the reaction was incomplete via TLC, another 0.5 eq tributyl(1-ethoxyvinyl)tin and 0.05 eq dichlorobis(triphenylphosphine)palladium (II) were added and the mixture was heated at reflux for overnight. The reaction mixture was cooled to room temperature and quenched with water and 10% HCl. After stirring at room temperature for 30 min, the mixture was extracted with ether. The combined ethereal layers were washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash chromatography (silica gel, 1% ethyl acetate in hexanes) gave a separable mixture of 1-(3-ethoxy-8-isopropyl-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-ethanone (Compound A-24) and the title compound.

Workup

  1. customAfter the mixture was degassed
  2. customvia bubbling argon for 30 min
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for 48 h
  5. temperaturethe mixture was heated
  6. temperatureat reflux for overnight
  7. customquenched with water and 10% HCl
  8. extractionthe mixture was extracted with ether
  9. washThe combined ethereal layers were washed with water and brine
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customPurification by flash chromatography (silica gel, 1% ethyl acetate in hexanes)
  14. customgave

Sources & evidence

ORD record
ord-cbca692829ff4e229a93f41487be9c13
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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