1,3-Dimethyl-2-imidazolidinone → HCID 178472355, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of cis/trans-4-(5-bromo-4-methyl-thiazol-2-yl)-cyclohexanecarboxylic acid ethyl ester (1:5) (371 mg, 1.12 mmol) and 2 M methyl zinc chloride solution in tetrahydrofuran (0.837 ml, 1.67 mmol) in a 5:1 mixture of tetrahydrofuran and 1,3-dimethyl-2-imidazolidinone (6 ml) was added (1,3-diisopropylimidazol-2-ylidene)(3-chloropyridyl)palladium(II) chloride (15.2 mg, 22.3 μmol) at room temperature. The reaction mixture was heated at 50° C. for 2 h. After cooling to room temperature the reaction mixture was partitioned between tert-butyl methyl ether (25 ml) and 0.1 M aqueous sodium hydroxide solution (25 ml). The layers were separated. The aqueous layer was extracted with two 25-ml portions of tert-butyl methyl ether. The combined organic layers were washed with two 25-ml portions of water, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification with n-heptane/ethyl acetate as eluent gave the title compound (170 mg, 57%) as colorless oil, with a purity of 80% according to GC. MS m/e: 268 ([M+H]+)

Provenance & Evidence