2-(Trimethylsiloxy)-1,3-butadiene → HCID 69612206, compound

HRID 1052197Notes

Reaction equation

HRID 1052197 reaction equation
[C:1]1([C:7]([NH:9][C:10](=[CH2:15])[C:11]([O:13][CH3:14])=[O:12])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si](C)(C)[O:18][C:19](=[CH2:22])[CH:20]=[CH2:21]>ClCCl.[I-].[Zn+2].[I-]>[O:18]=[C:19]1[CH2:20][CH2:21][C:10]([NH:9][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:8])([C:11]([O:13][CH3:14])=[O:12])[CH2:15][CH2:22]1

Participants

5

Reactant 2

HCID 5546572-(Trimethylsiloxy)-1,3-butadieneHCID 11745779HCID 11745779, compound

Product 1

HCID 69612206HCID 69612206, compound

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the crude product (67.0 g) of methyl 2-[(phenylcarbonyl)amino]prop-2-enoate produced above in dichloromethane (300 mL) was added zinc iodide (104 g). To the mixture was added trimethyl[(1-methylideneprop-2-en-1-yl)oxy]silane (173 mL), and the mixture was heated under reflux for 24 hr. The reaction system was allowed to cool to room temperature, washed with water, and dried over anhydrous sodium sulfate. Insoluble material was removed by filtration. To the filtrate were added a mixture (1:4, 40 mL) of 1M hydrochloric acid and tetrahydrofuran, and the mixture was stirred at room temperature for 5 hr. The reaction mixture was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (56.0 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hr
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customInsoluble material was removed by filtration
  6. additionTo the filtrate were added a mixture (1:4, 40 mL) of 1M hydrochloric acid and tetrahydrofuran
  7. washThe reaction mixture was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-bb6f3bc84b0e400e9a4f6d41461d6b7f
Source dataset
uspto-grants-2016_07
Patent number
US09388195B2

Reaction notes

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