Stannane, tributyl(1-ethoxyethenyl)- → HCID 22491007, compound

HRID 2180566Notes

Reaction equation

HRID 2180566 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:16])([CH3:15])[CH2:7][CH:8]=[C:9]2[CH:12]([CH3:14])[CH3:13])=[CH:4][C:3]=1[O:17][CH2:18][CH3:19].C([Sn](CCCC)(CCCC)[C:25]([O:27]CC)=[CH2:26])CCC>C1COCC1.O.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>[CH3:15][C:6]1([CH3:16])[C:5]2[C:10](=[CH:11][C:2]([C:25](=[O:27])[CH3:26])=[C:3]([O:17][CH2:18][CH3:19])[CH:4]=2)[C:9]([CH:12]([CH3:14])[CH3:13])=[CH:8][CH2:7]1

Participants

6

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 22218334HCID 22218334, compound

Product 1

HCID 22491007HCID 22491007, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution 7-bromo-4,4-dimethyl-6-ethoxy-1-isopropyl-3,4-dihydronaphthalene (Compound A-32, 284 mg, 0.879 mmol) in THF (5 mL) was tributyl(1-ethoxyvinyl) tin (0.445 mL, 1.32 mmol), and the resulting solution was purged with dry argon for 15 min. Dichlorobis(triphenylphosphine)palladium(II) (0.031 g, 0.044 mmol) was added and the solution was refluxed until the reaction was complete by TLC analysis. The reaction was cooled to room temperature. The mixture was diluted with water, extracted with ethyl ether, washed with brine, dried over MgSO4, and filtered. The solvent was removed under reduce pressure, and the residue was purified by flash column chromatography (silica gel, 95:5 hexane/ethyl acetate) to produce the title compound as a colorless solid.

Workup

  1. customthe resulting solution was purged with dry argon for 15 min
  2. temperaturethe solution was refluxed until the reaction
  3. extractionextracted with ethyl ether
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed
  8. customthe residue was purified by flash column chromatography (silica gel, 95:5 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b20865aeec6b48bfaa0c045f5ad862b3
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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