Tributylvinyltin → HCID 68527280, compound

HRID 1990101Notes

Reaction equation

HRID 1990101 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([S:20][CH3:21])=[C:9]([C:18]#[N:19])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1)=[O:5])[CH3:2].[CH2:22]([Sn](CCCC)(CCCC)C=C)[CH2:23]CC.[Li+].[Cl-]>C1COCC1.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:3][C:4]([C:6]1[S:7][C:8]([S:20][CH3:21])=[C:9]([C:18]#[N:19])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([CH:22]=[CH2:23])=[CH:13][CH:12]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 68524438HCID 68524438, compound

Product 1

HCID 68527280HCID 68527280, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Combine 4-cyano-3-(4-iodo-phenyl)-5-methylsulfanyl-thiophene-2-carboxylic acid ethyl ester (0.1 g, 1.0 eq) in THF (5.0 mL) and stir. Add Pd(PPh3)4 (1%), tributyl-vinyl-stannane (0.9 eq) and LiCl. Reflux the mixture overnight. Concentrate to dryness. Wash with hexane to remove excess of stannane. Add water and filter the precipitate to provide the title compound (0.04 g, Yield 38%). MS (ES+, m/e): 330 (M+1).

Workup

  1. temperatureReflux the mixture overnight
  2. concentrationConcentrate to dryness
  3. washWash with hexane
  4. customto remove excess of stannane
  5. filtrationAdd water and filter the precipitate

Sources & evidence

ORD record
ord-a1806c74323f4301b61ecf559a6c5f90
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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