Tetrahydrofuran → 2-(4-Formyl-3-methylphenyl)-2-methylpropanenitrile
Reaktionsgleichung
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[C:9]#[N:10])=[CH:4][C:3]=1[CH3:13].[Li]C(C)(C)C.C1C[O:22][CH2:21]C1>>[CH:21]([C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[C:9]#[N:10])=[CH:4][C:3]=1[CH3:13])=[O:22]Komponenten
4
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
2-(4-bromo-3-methylphenyl)-2-methylpropanenitrile (3.31 g, 13.9 mmol) is dissolved in dry THF (80 mL). The mixture is cooled to −78° C. and tert-BuLi (1.7 M in pentane, 18 mL, 30.6 mmol) is added. After 30 minutes, the reaction is quenched with DMF (10 mL), volatiles are evaporated and the residue purified by normal phase MPLC (SiO2, heptane to heptane/EtOAc 3:1), giving 2-(4-formyl-3-methylphenyl)-2-methylpropanenitrile (1.89 g, 10.2 mmol, 73%) as a colorless liquid. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.70 (s, 6H) 2.64 (s, 3H) 7.49 (s, 1H) 7.55 (dd, J=8.01, 2.15 Hz, 1H) 7.86 (d, J=7.81 Hz, 1H) 10.22 (s, 1H).