HCID 67048388, compound → HCID 67048369, compound

HRID 2094276Notes

Reaction equation

HRID 2094276 reaction equation
[CH2:1]([N:4]([C:16](=[O:21])[CH2:17][CH2:18][CH:19]=[CH2:20])[C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[CH3:15])C=C>C(=C1CCCC(P(Cl)(Cl)(C2CCCCC2)C2CCCCC2)C1=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)C1C=CC=CC=1.[Ru]>[N:4]1([C:5]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=2[CH3:15])[CH2:1][CH2:20][CH:19]=[CH:18][CH2:17][C:16]1=[O:21]

Participants

3

Reactant 1

HCID 67048388HCID 67048388, compound

Product 1

HCID 67048369HCID 67048369, compound

Reagents, catalysts & solvents 1

HCID 131726864HCID 131726864, compoundCatalyst

Procedure

150 mg (0.52 mmol) methyl 4-(allyl-pent-4-en-1-oyl-amino)-3-methyl-benzoate are dissolved in 110 ml degassed dichloromethane and rinsed for 30 minutes with argon. Then 88 mg (104 μmol) benzylidene-[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]-dichloro-(tricyclohexylphosphine)-ruthenium (2nd generation Grubbs Catalyst) are added and the mixture is refluxed for 4.5 hours. Then it is evaporated down i. vac., the residue is applied to silica gel and purified by chromatography on silica gel (eluant: petroleum ether/ethyl acetate 3:2).

Workup

  1. customdegassed dichloromethane
  2. washrinsed for 30 minutes with argon
  3. temperaturethe mixture is refluxed for 4.5 hours
  4. customThen it is evaporated down i
  5. custompurified by chromatography on silica gel (eluant: petroleum ether/ethyl acetate 3:2)

Sources & evidence

ORD record
ord-10c04bef570b446ea6923c195cb77228
Source dataset
uspto-grants-2013_05
Patent number
US08445525B2

Reaction notes

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