Acrylonitrile → Methyl Undecenoate Acrylonitrile

HRID 239233

Reaktionsgleichung

[C:1]([O:13][CH3:14])(=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[C:15](#[N:18])[CH:16]=[CH2:17].[Na].C(C1C=CC=CC=1)(=O)C1C=CC=CC=1.CCCCCCCCCCCC.C(C=CCCCCCCCCC(OC)=O)#N>CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3OC(C)C)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1.C1(C)C=CC=CC=1>[C:1]([O:13][CH3:14])(=[O:12])[CH:2]=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[C:15](#[N:18])[CH:16]=[CH2:17]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

100 mg of methyl 10-undecenoate (0.5 mmol), 53 mg of acrylonitrile (1 mmol) and 10 ml of toluene distilled over sodium-benzophenone are placed in a 50 ml Schlenk tube. 1.5 mg (2.4×10−3 mmol) of second-generation Hoveyda-Grubbs catalyst ((1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(o-iso-propoxyphenylmethylene)ruthenium, available from Aldrich) are added. The mixture is heated to 100° C. and left to react for 1 hour under nitrogen and with magnetic stirring. The reaction mixture is analyzed by gas chromatography (dodecane standard). The conversion of the methyl 10-undecenoate is 94%. The selectivity toward methyl 11-cyano-10-undecenoate (cis+trans mixture) is 100%. The TON (turnover number) is 188.

Aufarbeitung

customare placed in a 50 ml Schlenk tube
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customto react for 1 hour under nitrogen and with magnetic stirring

Quellen und Nachweise

ORD-Eintrag: ord-589628850163417e95244eef3e8ebf6c
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08642792B2

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