Tributylvinyltin → HCID 21476907, compound

HRID 2293580Notes

Reaction equation

HRID 2293580 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1OS(C(F)(F)F)(=O)=O)[C:7]([O:9][CH3:10])=[O:8])[CH2:2][CH3:3].[CH:22]([Sn](CCCC)(CCCC)CCCC)=[CH2:23]>CN(C=O)C.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>[CH2:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[CH:22]=[CH2:23])[C:7]([O:9][CH3:10])=[O:8])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 21476928HCID 21476928, compound

Product 1

HCID 21476907HCID 21476907, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 8.053 g (24.7 mmol) of the product of Step A and 8.136 g (25.7 mmol) of vinyltributyltin in 50 mL of anhydrous DMF was added 0.520 g (0.74 mmol) of bis(triphenylphosphine)palladium(II) chloride, the mixture was freed of air by alternate vacuum and nitrogen flush cycles, and the reaction mixture was magnetically stirred at 60° C. for 6 hours. The reaction mixture was then cooled to room temperature, partitioned between EtOAc and saturated brine, and extracted. The organic layer was washed three times with brine, separated, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 3% EtOAc in hexane. Evaporation of the purified fractions and drying in vacuo afforded 3.176 g (63%) of the title compound as a clear oil.

Workup

  1. customflush cycles
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. custompartitioned between EtOAc and saturated brine
  4. extractionextracted
  5. washThe organic layer was washed three times with brine
  6. customseparated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified on a silica gel flash chromatography column
  11. washeluted with 3% EtOAc in hexane
  12. customEvaporation of the purified fractions
  13. customdrying in vacuo

Sources & evidence

ORD record
ord-092bea7a989445a7aeb0425cee1eb2b2
Source dataset
uspto-grants-1997_11
Patent number
US05686478

Reaction notes

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