HCID 68494388, compound → HCID 68493128, compound

HRID 2242456Notes

Reaction equation

HRID 2242456 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[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:21]=3)[CH2:16][CH:15]2[C:38](=[O:46])[NH:39][CH2:40][CH2:41][CH2:42][CH2:43][CH:44]=[CH2:45])=[O:13])[CH2:8][CH:7]1C=C)=[O:5])[CH3:2]>ClCCl.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:45]=[CH:44][CH2:43][CH2:42][CH2:41][CH2:40][NH:39][C:38](=[O:46])[CH:15]1[CH:14]([CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:21]=3)[CH2:16]1)[C:12](=[O:13])[NH:11]2)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 68494388HCID 68494388, compound

Product 1

HCID 68493128HCID 68493128, compoundYield 32%

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 6344DichloromethaneSolvent

Procedure

Compound 91 (363 mg, 0.58 mmol) was dissolved in degassed dichloromethane (100 ml). Hoveyda-Grubbs catalyst 2nd generation (26 mg, 0.041 mmol) was added and the mixture was refluxed under argon atmosphere overnight. The reaction mixture was evaporated on silica and purified by silica gel chromatography (50% EtOAc in hexane→70% EtOAc in hexane) to give the pure title product (111 mg, 32%). MS (M+H+): 597.7

Workup

  1. temperaturethe mixture was refluxed under argon atmosphere overnight
  2. customThe reaction mixture was evaporated on silica
  3. custompurified by silica gel chromatography (50% EtOAc in hexane→70% EtOAc in hexane)

Sources & evidence

ORD record
ord-c311d5b2b7e1453b8fbf2749a10fc348
Source dataset
uspto-grants-2010_03
Patent number
US07671032B2

Reaction notes

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