Tributylvinyltin → HCID 18630129, compound

HRID 378096Notes

Reaction equation

HRID 378096 reaction equation
[Cl:1][C:2]1[C:12](I)=[CH:11][CH:10]=[C:9]([Si:14]([CH3:17])([CH3:16])[CH3:15])[C:3]=1[C:4]([NH:6][CH2:7][CH3:8])=[O:5].[CH:18]([Sn](CCCC)(CCCC)CCCC)=[CH2:19]>C1(C)C=CC=CC=1.CCOCC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>[Cl:1][C:2]1[C:12]([CH:18]=[CH2:19])=[CH:11][CH:10]=[C:9]([Si:14]([CH3:17])([CH3:16])[CH3:15])[C:3]=1[C:4]([NH:6][CH2:7][CH3:8])=[O:5]

Participants

7

Reactant 2

HCID 81998TributylvinyltinHCID 10523923HCID 10523923, compound

Product 1

HCID 18630129HCID 18630129, compoundYield 21.3%

Reagents, catalysts & solvents 4

HCID 314042,6-Di-tert-butyl-4-methylphenolCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst2×HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of the compound of Example 239 (0.382 g, 1.0 mmol), tetrakis(triphenylphosphine)-palladium(O) (23 mg, 0.02 mmol) and 2.6-di-t-butyl-4-methylphenol (1.5 mg) in toluene (10 mL) was added vinyltributyltin (0.349 g, 1.1 mmol). The light yellow solution was heated at reflux for 24 h, additional tetrakis(triphenylphosphine)palladium(O) (15 mg) was added, and reflux was continued for 24 h. The cool mixture was diluted with ether, filtered through Celite, concentrated and purified by RC (ethyl acetate/hexanes). The product was further purified by recrystallization from pentane to afford the title compound as white needles (0.060 g, 21%). m.p. 127-128° C.

Workup

  1. temperatureThe light yellow solution was heated
  2. temperatureat reflux for 24 h
  3. temperaturereflux
  4. filtrationfiltered through Celite
  5. concentrationconcentrated
  6. custompurified by RC (ethyl acetate/hexanes)
  7. customThe product was further purified by recrystallization from pentane

Sources & evidence

ORD record
ord-ca2cdc49e48f42808c8e1d99f4bc293d
Source dataset
uspto-grants-2000_02
Patent number
US06028101

Reaction notes

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