HCID 58873061, Verbindung → 3-(4-tert-Butyl-phenyl)-4-cyano-5-ethyl-thiophene-2-carboxylic acid ethyl ester
Reaktionsgleichung
C([Zn][CH2:4][CH3:5])C.[CH2:6]([O:8][C:9]([C:11]1[S:12][C:13](S(C)(=O)=O)=[C:14]([C:26]#[N:27])[C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=1)=[O:10])[CH3:7]>C(Cl)Cl>[CH2:6]([O:8][C:9]([C:11]1[S:12][C:13]([CH2:4][CH3:5])=[C:14]([C:26]#[N:27])[C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH3:24])([CH3:23])[CH3:25])=[CH:18][CH:17]=1)=[O:10])[CH3:7]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Add diethylzinc (1.0M in hexanes, 16 mL, 16 mmol) to a solution of 3-(4-tert-butyl-phenyl)-4-cyano-5-methanesulfonyl-thiophene-2-carboxylic acid ethyl ester (2.78 mmol) in 15 mL of anhydrous CH2Cl2 and stir under nitrogen at room temperature for 5 days. Cool to 0° C. and carefully quench with ice followed by 10 mL of saturated NH4Cl. Filter the mixture through Celite® and rinse the filter pad with 100 mL of CH2Cl2. Wash the combined organic layers with brine (1×20 mL), dry over Na2SO4, filter and evaporate. Chromatograph over silica gel with 100% toluene to give the title compound as a clear oil, 625 mg (66%). MS (FAB)=341 (M+); HPLC=98%.