1,3-Dimethyl-2-imidazolidinone → HCID 178501071, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of trans-4-(4-bromo-5-methyl-isoxazol-3-yl)-cyclohexanecarboxylic acid methyl ester (660 mg, 2.18 mmol) and 2 M methyl zinc chloride solution in tetrahydrofuran (1.64 ml, 3.28 mmol) in a 4:1 mixture of tetrahydrofuran and 1,3-dimethyl-2-imidazolidinone (12 ml) was added (1,3-diisopropylimidazol-2-ylidene)(3-chloropyridyl)palladium(II) chloride (29.7 mg, 43.7 μmol) at room temperature. The reaction mixture was heated at 50° C. for 2 h. The reaction mixture was partitioned between tert-butyl methyl ether (100 ml) and 0.1 M aqueous hydrochloric acid solution (100 ml). The layers were separated. The aqueous layer was extracted with one 100 ml-portion of tert-butyl methyl ether. The combined organic layers were washed with two 50 ml-portions of water and one 50-ml portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification with n-heptane/ethyl acetate as eluent gave the title compound (460 mg, 84%) as light yellow oil, with a purity of 90% according to GC. MS m/e: 238 ([M+H]+)

Provenance & Evidence