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

HRID 1662466

反応式

[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

参加物

反応条件

温度: 55 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード: ord-6bdae972316d4ef39d8fa7e3e551bd8d
出典データセット: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08030354B2

反応式

参加物

反応物 2

生成物 1

試薬・触媒・溶媒 2

反応条件

実験手順

後処理

出典と根拠

関連ノート