HCID 68590970, compound → HCID 68590866, compound

HRID 1429162Notes

Reaction equation

HRID 1429162 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[CH:25]=[C:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:23]=[C:22]([O:32][CH3:33])[N:21]=3)[CH2:16][CH:15]2[C:34](=[O:43])[N:35]([CH2:37][CH2:38][CH2:39][CH2:40]C=C)[CH3:36])=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]>ClCCCl.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3OC(C)C)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1>[CH2:1]([O:3][C:4]([C:6]12[CH2:8][CH:7]1[CH:9]=[CH:10][CH2:40][CH2:39][CH2:38][CH2:37][N:35]([CH3:36])[C:34](=[O:43])[CH:15]1[CH:14]([CH2:18][CH:17]([O:19][C:20]3[CH:25]=[C:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:23]=[C:22]([O:32][CH3:33])[N:21]=3)[CH2:16]1)[C:12](=[O:13])[NH:11]2)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 68590970HCID 68590970, compound

Product 1

HCID 68590866HCID 68590866, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 11763533(1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)rutheniumCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a solution of the diolefin 13c (760 mg, 1.28 mmol) in DCE (700 ml) under argon (three times evaporated three times filled with argon) was added Hoveyda Grubbs catalyst 2nd generation (80 mg) and the mixture was refluxed overnight. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography with hexane ethyl acetate which gave the title compound (0.52 g, 70%), (M+H)+563.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel chromatography with hexane ethyl acetate which

Sources & evidence

ORD record
ord-954fa6f7c71142299a85d9362fd85764
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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