3,4-dihydro-2H-pyran → HCID 71272225, compound

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Reaction Steps

A mixture of 5-bromo-6-methyl-1H-benzo[d]imidazole (2.0 g, 9.6 mmol), p-TsOH (17 mg, 0.1 mmol), and dihydropyran (8.1 g, 96 mmol) in THF (30 mL) was heated to reflux overnight. The solvent was concentrated in vacuo and EtOAc (50 mL) and water (50 mL) were added to the residue. The pH was adjusted to about 8 with K2CO3. The aqueous phase was extracted with EtOAc (50 mL×2). The combined organic layers were washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (2:1) to afford 5-bromo-6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole as a yellow solid (2.1 g, 71%). MS (ESI): m/z=295.2 [M+1]+.

Provenance & Evidence