Tributylvinyltin → HCID 19592870, compound

HRID 613464Notes

Reaction equation

HRID 613464 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[C:9]2OS(C(F)(F)F)(=O)=O)([O-:3])=[O:2].[CH2:22]([Sn](CCCC)(CCCC)C=C)[CH2:23]CC.[Cl-].[Li+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[C:9]2[CH:22]=[CH2:23])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 19592735HCID 19592735, compound

Product 1

HCID 19592870HCID 19592870, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 8-nitro-4-(trifluoromethanesulfonyloxy)quinoline (6.0 g), tri-n-butyl(vinyl)tin (6.49 g), tetrakis(triphenylphosphine)palladium(0) (1.08 g) and lithium chloride (2.37 g) in dioxane (120 ml) was refluxed for 1.5 hours. The mixture was concentrated in vacuo, and ethyl acetate (200 ml) was added to the residue. The mixture was stirred for 1 hour, and insoluble material was filtered off. The residue was purified by flash chromatography (ethyl acetate-n-hexane) to give 8-nitro-4-vinylquinoline (2.39 g).

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. concentrationThe mixture was concentrated in vacuo, and ethyl acetate (200 ml)
  3. additionwas added to the residue
  4. filtrationinsoluble material was filtered off
  5. customThe residue was purified by flash chromatography (ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-e1f03fac209d47ba9d1feef3e2b713f8
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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