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

HRID 404388

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

Conditions

Temperature: 55 °C

Procedure

To a solution of methyl 4-(allyloxy)benzoate 26.1 (3.00 g, 16.0 mmol) and methylenecyclopentane (1.9 g, 23.0 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) in DCM (5.0 mL) was added Hoveyda-Grubbs reagent (0.39 g, 0.62 mmol), (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) at room temperature. The resulting reaction mixture was degassed three times and then stirred at 55° C. under nitrogen overnight. The reaction mixture was purified by CombiFlash® silica gel column chromatography (hexane/EtOAc 95/5) to give 26.2, (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

customat room temperature
customThe resulting reaction mixture
customwas degassed three times
customThe reaction mixture was purified by CombiFlash® silica gel column chromatography (hexane/EtOAc 95/5)

Sources & evidence

ORD record: ord-112f4ea5ec9945a191d959619a18a4be
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748462B2

Linked notes

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