Tributylvinyltin → HCID 22037878, compound

HRID 1790379Notes

Reaction equation

HRID 1790379 reaction equation
[CH:1]([NH:4][C:5](=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1)([CH3:3])[CH3:2].[CH:15]([Sn](CCCC)(CCCC)CCCC)=[CH2:16]>C1(C)C=CC=CC=1.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>[CH:1]([NH:4][C:5](=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:15]=[CH2:16])=[CH:9][CH:8]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 81998TributylvinyltinHCID 669886HCID 669886, compound

Product 1

HCID 22037878HCID 22037878, compoundYield 72.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Isopropyl-4-bromophenylacetamide (1.0 g) and vinyltributyltin (1.4 ml) were dissolved in toluene (12 ml). After adding tetrakistriphenylphosphinepalladium (0.5 g) thereto, the resultant mixture was heated under reflux for 4 hr. Then it was allowed to cool and diluted with ethyl acetate. The resulting solid was filtered off and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate system) to give colorless crystals (0.578 g) of the title compound (yield: 72.8%).

Workup

  1. temperatureunder reflux for 4 hr
  2. temperatureto cool
  3. filtrationThe resulting solid was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-b94034fa01654e1fbaf9e8144889e1a6
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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