Iodoethane → Methyl 4-(3-cyanopentan-3-yl)benzoate

Reaktionsgleichung

C[C:2]([CH3:5])([O-])C.[K+].[CH2:7](I)[CH3:8].[C:10]([CH2:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)#[N:11]>C1COCC1>[C:10]([C:12]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)([CH2:2][CH3:5])[CH2:7][CH3:8])#[N:11]

Komponenten

Versuchsvorschrift

To a solution of potassium tert-butoxide (4.81 g) in THF (15 mL) at −30° C. was added a solution of ethyl iodide (4.11 mL) and methyl 4-(cyanomethyl)benzoate (3 g) THF (15 mL) under nitrogen atmosphere over 20 min. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The reaction was quenched by the addition of water (10 mL) and ethyl acetate was added. The organic layer was washed successively with water, brine and dried over anhydrous sodium sulfate. The organic solvent was removed to obtain a residue, which was purified by column chromatography (silicagel, 20% ethyl acetate in petroleum ether) to obtain a crude solid. The crude solid was crystallized using chloroform in petroleum ether to afford the title compound.