Citric Acid → HCID 71272657, compound

Participants

Reaction Steps

To a solution of 6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-5-carbonitrile (1.1 g, 4.6 mmol) in anhydrous THF (20 mL) under nitrogen at 0° C. was dropped a solution of CH3MgBr in THF (8 mL, 24 mmol) at a rate that the internal reaction temperature remained below 10° C. After the addition, the reaction mixture was stirred at RT overnight. The mixture was slowly poured into ice-water (20 mL) and stirred at RT for 0.5 h. The solution's pH was adjusted to 5.0˜6.0 by using citric acid, and mixture was extracted with EtOAc (20 mL×3). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (1:1) to afford 1-(6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)ethanone as a yellow solid (1.1 g, 90.1%). MS (ESI): m/z=259.2 [M+1]+.

Provenance & Evidence