Cyclopentane, methylene- → Methyl 4-(2-cyclopentylideneethoxy)benzoate

HRID 1662466

Reaction equation

HRID 1662466 reaction equation
[CH2:1]([O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[CH2:15]=[C:16]1CC[CH2:18][CH2:17]1>C(Cl)Cl.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C(OC(C)C)=CC=CC=3)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1>[C:3]1(=[CH:2][CH2:1][O:4][C:5]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 73714Cyclopentane, methylene-HCID 4645407Methyl 4-(allyloxy)benzoate

Product 1

HCID 57467652Methyl 4-(2-cyclopentylideneethoxy)benzoateYield 68%

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

Conditions

Temperature
55 °C

Procedure

To a solution of methyl 4-(allyloxy)benzoate 66.67A (3.00 g, 16.0 mmol) and methylenecyclopentane (1.9 g, 23.0 mmol) in DCM (5.0 mL) was added Hoveyda Grubbs reagent (0.39 g, 0.62 mmol) at room temperature. The resulting reaction mixture was degassed three times and stirred at 55° C. under nitrogen overnight. The reaction mixture was purified by Combi Flash silica gel chromatography (hexane/EtOAc 95/5) to give the compound 66.67B, (2.60 g, yield 68%). 1H NMR (500 MHz, CDCl3) δ ppm 7.82-7.93 (2H, m), 6.80-6.88 (2H, m), 5.44-5.56 (1H, m), 4.47 (2H, d, J=6.6 Hz), 3.80 (3H, s), 2.20-2.31 (4H, m), 1.50-1.71 (4H, m).

Workup

  1. customThe resulting reaction mixture
  2. customwas degassed three times
  3. customThe reaction mixture was purified by Combi Flash silica gel chromatography (hexane/EtOAc 95/5)

Sources & evidence

ORD record
ord-6bdae972316d4ef39d8fa7e3e551bd8d
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Linked notes

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