HCID 59356046, compound → HCID 67484581, compound

HRID 660989Notes

Reaction equation

HRID 660989 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10]([CH2:34]C=C)([CH2:14][O:15][C:16]2[CH:21]=[C:20]([CH3:22])[C:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[C:18]([CH3:33])[CH:17]=2)[CH2:11][CH:12]=[CH2:13])=[CH:8][CH:9]=1)=[O:4]>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>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10]2([CH2:14][O:15][C:16]3[CH:17]=[C:18]([CH3:33])[C:19]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)=[C:20]([CH3:22])[CH:21]=3)[CH2:34][CH:13]=[CH:12][CH2:11]2)=[CH:8][CH:9]=1)=[O:4]

Participants

4

Reactant 1

HCID 59356046HCID 59356046, compound

Product 1

HCID 67484581HCID 67484581, compoundYield 87%

Reagents, catalysts & solvents 2

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

Procedure

A solution of 5-[1-allyl-1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-thiophene-2-carboxylic acid methyl ester (0.292 g, 0.567 mmol) in CH2Cl2 (270 mL) is treated with [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)-(tricyclohexylphosphine)ruthenium] (0.0528 g, 0.0622 mmol) for 4 h and concentrated. The residue is loaded onto silica gel and eluted using hexanes with an ethyl acetate gradient from 0% to 40% to afford 5-[1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxymethyl)-cyclopent-3-enyl]-thiophene-2-carboxylic acid methyl ester (0.240 g, 87%) as a colorless syrup. MS (ES): 487.4 [M+H]+.

Workup

  1. concentrationconcentrated
  2. washeluted

Sources & evidence

ORD record
ord-c7f3aaa6015e4b1eb97003dec4086bec
Source dataset
uspto-grants-2011_12
Patent number
US08084489B2

Reaction notes

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