HCID 86631214, compound → HCID 86631215, compound

HRID 253017Notes

Reaction equation

HRID 253017 reaction equation
C=[C:2]([CH2:26][CH2:27][CH3:28])[CH2:3][CH2:4][N:5]([C@@H:18]([CH2:23][CH:24]=C)[C:19]([O:21][CH3:22])=[O:20])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7]>C(Cl)Cl.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1>[N+:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[S:6]([N:5]1[CH2:4][CH2:3][C:2]([CH2:26][CH2:27][CH3:28])=[CH:24][CH2:23][C@H:18]1[C:19]([O:21][CH3:22])=[O:20])(=[O:8])=[O:7])([O-:17])=[O:16]

Participants

4

Reactant 1

HCID 86631214HCID 86631214, compound

Product 1

HCID 86631215HCID 86631215, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 11147261(1,3-Dimesitylimidazolidin-2-ylidene)(tricyclohexylphosphine)benzylidene ruthenium dichlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Benzylidene[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(tricyclohexylphosphine)ruthenium (250 mg, 0.295 mmol) was added to a solution of 2.42 g (5.89 mmol) of the title compound produced in step (iii) of Example 47 in methylene chloride (295 ml), and the mixture was heated under reflux for one hr. The reaction solution was cooled to room temperature, and the solvent was removed under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1) to give 1.84 g (yield 82%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for one hr
  3. customthe solvent was removed under the reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-0e8c165c80d44013a534d4718e2784c2
Source dataset
uspto-grants-2011_01
Patent number
US07871982B2

Reaction notes

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