Boron trifluoride etherate → 2-(2-(4-Fluorophenyl)oxazol-4-yl)-2-methoxyacetonitrile

Reaktionsgleichung

C[Si]([C:5]#[N:6])(C)C.[CH3:7][O:8][CH:9](OC)[C:10]1[N:11]=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[O:13][CH:14]=1.B(F)(F)F.CCOCC>>[F:21][C:18]1[CH:17]=[CH:16][C:15]([C:12]2[O:13][CH:14]=[C:10]([CH:9]([O:8][CH3:7])[C:5]#[N:6])[N:11]=2)=[CH:20][CH:19]=1

Komponenten

Edukt 3

HCID 8000Boron trifluoride etherate

HCID 82115Trimethylsilyl cyanide

HCID 673246204-(Dimethoxymethyl)-2-(4-fluorophenyl)oxazole

Produkt 1

HCID 673263782-(2-(4-Fluorophenyl)oxazol-4-yl)-2-methoxyacetonitrileAusbeute 25,5 %

Versuchsvorschrift

Trimethylsilyl cyanide (4.13 g, 41.76 mmol) was added to a solution of 4-(dimethoxymethyl)-2-(4-fluorophenyl)oxazole (400 mg, 1.69 mmol) at room temperature, followed by boron trifluoride diethyl etherate (37 mg, 0.26 mmol). The reaction mixture was stirred for 20 min, quenched with saturated aqueous NaHCO3 solution, and extracted with EtOAc. The combined extracts were washed with H2O and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 8-10% EtOAc in petroleum ether) to afford 2-(2-(4-fluorophenyl)oxazol-4-yl)-2-methoxyacetonitrile (100 mg, yield 16%) as a light yellow liquid. 1H NMR (400 MHz, CDCl3) δ 8.08-8.06 (m, 2H), 7.90 (d, J=0.9 Hz, 1H), 7.19-7.15 (m, 2H), 5.29 (d, J=0.9 Hz, 1H), 3.62 (s, 3H). MS (ESI) m/z: Calculated for C12H9FN2O2: 232.21. found: 232.9 (M+H)+.