2-Methyl-2-butene → HCID 178440112, compound

Participants

Reaction Steps

A solution of sodium chlorite (2.9 g, 32.1 mmol) and sodium dihydrogen phosphate monohydrate (2.5 g, 18.1 mmol) in water (7.2 mL) was added to a stirred solution of 4-chloro-2-propyl-1H-imidazole-5-carbaldehyde (0.541 g, 3.1 mmol), 2-methyl-2-butene (19.3 mL of a 2M solution in THF, 38.6 mmol), and tert-butanol (2.3 mL) in THF (10 mL). The reaction mixture was stirred at RT for 6 h. The aqueous phase was separated and extracted with EtOAc (4×40 mL). The combined extracts were dried (Na2SO4), filtered, concentrated and the residue was triturated with diethyl ether to provide the title compound (0.587 g, quant.) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.99 (br. s., 1H), 12.88, (br. s., 1H), 2.55 (t, 2H), 1.63 (sex, 2H), 0.86 (t, 3H). ES-LCMS: m/z 189.0 (M+H).

Provenance & Evidence