4-[1-Allyl-1-(2,6-dimethyl-4'-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoic acid methyl ester → 4-[1-(2,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-yloxymethyl)-cyclopent-3-enyl]-benzoic acid methyl ester

HRID 658293Notes

Reaction equation

HRID 658293 reaction equation
[CH3:1][O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:34][CH:35]=[CH2:36])([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]C=C)=[CH:6][CH:5]=1>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](=[O:37])[C:4]1[CH:9]=[CH:8][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:30])([F:32])[F:31])=[CH:25][CH:24]=4)=[C:20]([CH3:22])[CH:21]=3)[CH2:11][CH:36]=[CH:35][CH2:34]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 674857174-[1-Allyl-1-(2,6-dimethyl-4'-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoic acid methyl ester

Product 1

HCID 674859244-[1-(2,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-yloxymethyl)-cyclopent-3-enyl]-benzoic acid methyl esterYield 84%

Reagents, catalysts & solvents 2

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

Procedure

A solution of 4-[1-allyl-1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoic acid methyl ester (6.0 mL of 0.11M stock solution in CH2Cl2, 0.578 g, 1.14 mmol) in CH2Cl2 (570 mL) is treated with [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)-(tricyclohexylphosphine)ruthenium] (0.101 g, 0.1192 mmol) at 35° C. for 1 h, cooled to room temperature, and concentrated. The residue is loaded onto silica gel and eluted using hexanes with an ethyl acetate gradient from 0% to 40% to afford the title compound (0.458 g, 84%) as a colorless syrup. 1H NMR (CDCl3): δ 7.98-7.96 (m, 2H), 7.63 (d, J=8.3 Hz, 2H), 7.44-7.41 (m, 2H), 7.20 (d, J=8.1 Hz, 2H), 6.58 (s, 2H), 5.77 (s, 2H), 3.99 (s, 2H), 3.89 (s, 3H), 2.87 (d, J=14.3 Hz, 2H), 2.77 (d, J=14.9 Hz, 2H), 1.92 (s, 6H).

Workup

  1. concentrationconcentrated
  2. washeluted

Sources & evidence

ORD record
ord-fbc8a4a7ec5643bb91d0e993776b061d
Source dataset
uspto-grants-2011_12
Patent number
US08076374B2

Reaction notes

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