7-(1-Allylbut-3-enyl)-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile → 7-(Cyclopent-3-enyl)-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Reaktionsgleichung

[CH2:1]([CH:4]([C:8]1[C:9]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:10]([CH3:22])[C:11]([C:20]#[N:21])=[C:12]2[C:16]=1[O:15][C:14]([CH:17]1[CH2:19][CH2:18]1)=[N:13]2)[CH2:5][CH:6]=[CH2:7])C=C>Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1.ClCCl>[CH:4]1([C:8]2[C:9]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:10]([CH3:22])[C:11]([C:20]#[N:21])=[C:12]3[C:16]=2[O:15][C:14]([CH:17]2[CH2:19][CH2:18]2)=[N:13]3)[CH2:5][CH:6]=[CH:7][CH2:1]1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

At room temperature, Grubbs catalyst second generation (92 mg, 0.11 mol) was added to a solution of 7-(1-allylbut-3-enyl)-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-299) (400 mg, 1.09 mmol) dissolved in dichloromethane; (108 ml). Under nitrogen atmosphere, the solution was stirred at 50° C. for 3.5 hours. After cooling to room temperature, the solvent was evaporated away under reduced pressure. The residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=9:1, v/v) to obtain the entitled compound (282 mg, 76%) as a white solid.

Aufarbeitung

temperatureAfter cooling to room temperature
customthe solvent was evaporated away under reduced pressure
customThe residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

Quellen und Nachweise

ORD-Eintrag: ord-76c1cd1e388e41eb867e36c7cd14dc26
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07737166B2

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