Tributylvinyltin → HCID 19603510, compound

HRID 1604577Notes

Reaction equation

HRID 1604577 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[C:14]2OS(C(F)(F)F)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:28]([Sn](CCCC)(CCCC)CCCC)=[CH2:29].[Cl-].[Li+]>O1CCOCC1.C(OCC)(=O)C.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>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[C:14]2[CH:28]=[CH2:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 19603266HCID 19603266, compound

Product 1

HCID 19603510HCID 19603510, compoundYield 52.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 8-benzyloxy-2-methyl-4-(trifluoromethanesulfonyloxy)quinoline (300 mg), vinyltributyltin (263 mg), tetrakis(triphenylphosphine)palladium (0) (43.6 mg) and lithium chloride (96 mg) in 1,4-dioxane (6 ml) was refluxed for three hours and then left at ambient temperature overnight. The mixture was diluted with ethyl acetate and was added silica gel (70-230 mesh, 5 g) and stirred at ambient temperature for half an hour. The silica gel was removed by filtration and the filtrate was concentrated in vacuo. The residue was chromatographed on a silica gel column eluting with ethyl acetate-n-hexane (1:4, V/V) to give a solid. This solid was crystallized from diisopropyl ether to give 8-benzyloxy-2-methyl-4-vinylquinoline (110 mg) as pale yellow solid.

Workup

  1. temperaturewas refluxed for three hours
  2. additionwas added silica gel (70-230 mesh, 5 g)
  3. customThe silica gel was removed by filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was chromatographed on a silica gel column
  6. washeluting with ethyl acetate-n-hexane (1:4, V/V)
  7. customto give a solid
  8. customThis solid was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-ada9566638ee4135b30a104ff0b0b9c9
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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