Lithium Chloride → 2-Phenyl-3-methyl-8-vinylquinoline

HRID 1167179Notes

Reaction equation

HRID 1167179 reaction equation
[Cl-].[Li+].[CH2:3](C([Sn])=C(CCCC)CCCC)[CH2:4]CC.[C:18]1([C:24]2[C:33]([CH3:34])=[CH:32][C:31]3[C:26](=[C:27](OS(C(F)(F)F)(=O)=O)[CH:28]=[CH:29][CH:30]=3)[N:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>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>[C:18]1([C:24]2[C:33]([CH3:34])=[CH:32][C:31]3[C:26](=[C:27]([CH:3]=[CH2:4])[CH:28]=[CH:29][CH:30]=3)[N:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 155214792-Phenyl-3-methyl-8-trifluoromethanesulfonyloxyquinolineHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 229959252-Phenyl-3-methyl-8-vinylquinolineYield 96%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

6.3 g (150 mmol) of lithium chloride, 16.8 ml (57 mmol) of tributylvinyltin and 1.6 g (1.5 mmol) of Pd(PPh3)4 are added sequentially at ambient temperature to a solution of 17.7 g (48 mmol) of 2-phenyl-3-methyl-8-trifluoromethanesulfonyloxyquinoline in 250 ml of dioxane, degassed beforehand using a stream of nitrogen. The reaction medium is then heated at 110° C. for 16 hours. After evaporating the dioxane, the residue is taken up in 200 ml of water and 200 ml of ethyl acetate. The aqueous phase is extracted with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue is purified by silica gel chromatography (eluent: ethyl acetate/cyclohexane 3/7) to provide 11.3 g of 2-phenyl-3-methyl-8-vinylquinoline in the form of a colorless oil. (Yield: 96%)

Workup

  1. customdegassed
  2. customAfter evaporating the dioxane
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified by silica gel chromatography (eluent: ethyl acetate/cyclohexane 3/7)

Sources & evidence

ORD record
ord-3b7055f1a163408db7d21a694642bc11
Source dataset
uspto-grants-2003_09
Patent number
US06617336B1

Reaction notes

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