Tetrahydrofuran → HCID 68486336, compound

Participants

Reaction Steps

A solution of 4-methyl-2-(1-methylethyl)-1H-imidazole-5-carboxylate (83 mg, 0.42 mmol) in THF (2.0 mL) was added dropwise to a suspension of NaH (60% in oil, 19.2 mg, 0.47 mmol) in THF (3.0 mL) at 0° C. under N2. The mixture was allowed warm up to room temperature and stirred for 2 h, it was then cooled to 0° C. and {2-[(chloromethyl)oxy]ethyl}(trimethyl)silane (84 uL, 0.47 mmol) was added dropwise. The mixture was stirred overnight at room temperature and saturated sodium bicarbonate was added. DCM was added and the organic layer was dried over sodium sulfate and concentrated. The residue was purified by column chromatography (0-2% 2M NH3 solution of MeOH in DCM) to give the title compound (133 mg, 96%) as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 5.16 (2H, s) 4.34 (2H, q, J=7.1 Hz) 3.44-3.51 (2H, m) 3.06 (1H, dt, J=13.8, 6.9 Hz) 2.54 (3H, s) 1.30-1.39 (9H, m) 0.84-0.92 (2H, m) −0.07-−0.02 (9H, m). LCMS: m/z 327 (M+1).

Provenance & Evidence