Tributylvinyltin → HCID 18007943, compound

HRID 429771Notes

Reaction equation

HRID 429771 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[C:7]([CH2:10][CH2:11][NH:12][C:13]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[O:14])[C:6]=2[CH:21]=1.[CH:22]([Sn](CCCC)(CCCC)CCCC)=[CH2:23]>CN1CCCC1=O.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>[CH:22]([C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[C:7]([CH2:10][CH2:11][NH:12][C:13]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[O:14])[C:6]=2[CH:21]=1)=[CH2:23]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 18007991HCID 18007991, compound

Product 1

HCID 18007943HCID 18007943, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

15 mmol of the product obtained in Step C, 16 mmol of vinyl tributyltin and 0.43 mmol of tetrakis(triphenylphosphine)palladium, are heated at 110° C., with stirring, for 3 hours in 30 ml of N-methylpyrrolidinone. After removal of the solvent by evaporation, the residue is taken up in 20 ml of dichloromethane and treated with an aqueous 10% potassium fluoride solution. Extraction, concentration under reduced pressure and chromatography over silica gel yield the pure title product.

Workup

  1. customAfter removal of the solvent
  2. customby evaporation
  3. additiontreated with an aqueous 10% potassium fluoride solution
  4. extractionExtraction, concentration under reduced pressure and chromatography over silica gel

Sources & evidence

ORD record
ord-565a0f1c262c418eb2e1414162291add
Source dataset
uspto-grants-2001_11
Patent number
US06319930B1

Reaction notes

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