Reaktionsgleichung
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([C:8]#[N:9])=[O:7])=[CH:4][CH:3]=1.[CH3:12][N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][C:19]([O:21][CH3:22])=[O:20].ClC(Cl)(Cl)C(O)=O>CCOCC>[C:8]([C:6]([OH:7])([C:5]1[CH:10]=[CH:11][C:2]([CH3:1])=[CH:3][CH:4]=1)[C:17]1[N:13]([CH3:12])[C:14]([CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:16]=1)#[N:9]Komponenten
Versuchsvorschrift
A solution of 1.45 g (0.01 mole) of 4-methylbenzoylcyanide, 1.5 g (0.01 mole) of methyl 1-methylpyrrole-2-acetate and 40 mg (0.25 mmoles) of trichloroacetic acid in 4 ml of ether was stirred at 25° under nitrogen for 21 days. The precipitated solid was collected by filtration and washed with cold ether, than hexane. The combined filtrates were evaporated in vacuo. A second crop of crystals was taken from hexane. After recrystallization from toluene:hexane was obtained, 0.46 g (16 percent yield) of methyl 5-[cyanohydroxy(4-methylphenyl)-methyl]-1-methylpyrrole-2-acetate mp 117°-118°. H1NMR CDCl3 2.35 (s, 3 H); 3.35 (s, 3 H); 3.55 (s, 2H); 3.65 (s, 3 H); 5.90 (d, 1 H); 6.05 (d, 1H); 7.15 (d, 2H); 7.35 (d, 2H). MS m/e 281, 280, 266, 212 IRnujol 3425, 1700 cm-1.
Aufarbeitung
- filtrationThe precipitated solid was collected by filtration
- washwashed with cold ether, than hexane
- customThe combined filtrates were evaporated in vacuo
- customAfter recrystallization from toluene
- customhexane was obtained
Quellen und Nachweise
- ORD-Eintrag
- ord-b2dca4c3d0d54749a8892380e6b6ad9b
- Quelldatensatz
- uspto-grants-1981_10
- Patentnummer
- US04294760
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