2-Methyl-2-butene → HCID 178441713, compound

Participants

Reaction Steps

A solution of sodium chlorite (2.0 g, 21.6 mmol) and sodium dihydrogen phosphate monohydrate (1.8 g, 12.9 mmol) in water (4.8 mL) was added to a stirred solution of 4-chloro-2-butyl-1H-imidazole-5-carbaldehyde (0.400 g, 2.1 mmol), 2-methyl-2-butene (13.4 mL of a 2M solution in THF, 26.8 mmol), and tert-butanol (1.6 mL) in THF (6.7 mL). The reaction mixture was stirred at RT for 12 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 (0.411 g, 95%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.99 (br. s., 1H), 12.88, (br. s., 1H), 2.58 (t, 2H), 1.59 (quint, 2 H), 1.20-1.31 (sex, 2H), 0.87 (t, 3H). ES-LCMS: m/z 203.1 (M+H).

Provenance & Evidence