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

HRID 1662466

반응식

HRID 1662466 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 11763533(1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)ruthenium촉매HCID 6344Dichloromethane용매

반응 조건

온도
55 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-6bdae972316d4ef39d8fa7e3e551bd8d
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030354B2

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