Lithium borohydride → 5-Fluoro-4-(2-hydroxyethyl)-2-methoxybenzonitrile
Reaktionsgleichung
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([C:13]#[N:14])=[CH:7][C:6]=1[F:15].[BH4-].[Li+]>O1CCCC1>[F:15][C:6]1[C:5]([CH2:4][CH2:3][OH:2])=[CH:10][C:9]([O:11][CH3:12])=[C:8]([CH:7]=1)[C:13]#[N:14]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of methyl(4-cyano-2-fluoro-5-methoxyphenyl)acetate (212 mg, 0.95 mmol) in tetrahydrofuran (4 mL) at 0° C. was added lithium borohydride (2.0 M solution in tetrahydrofuran, 0.62 mL). The mixture warmed slowly to room temperature and was quenched with saturated sodium bicarbonate and diluted with ethyl acetate. The layers were separated and the aqueous extracted with ethyl acetate (2×). The combined organics were washed with water and brine, then dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography (MPLC, 5-60% Ethyl Acetate:Hexanes) to provide 5-fluoro-4-(2-hydroxyethyl)-2-methoxybenzonitrile. 1H-NMR (500 MHz, CD3OD) δ ppm 7.22 (m, 1H), 6.92 (m, 1H), 3.93 (s, 3H), 3.88 (m, 2H), 2.95 (m, 2H), 2.29 (br s, 1H).