Potassium Hydroxide → HCID 70980533, compound

Participants

Reaction Steps

Ethyl 2-methyl-1H-imidazole-4-carboxylate (1.622 mmol, 250 mg) and KOH (2.432 mmol, 136 mg) were suspended in DMF (2 ml). 1,1-Difluoro-2-iodoethane (4.86 mmol, 934 mg) was added and the resulting mixture was stirred overnight at RT. During the stirring additional 0.3 ml of 1,1-difluoro-2-iodoethane was added to complete the reaction. Aqueous NH4Cl solution was added and the mixture was extracted three times with EtOAc. The combined organics were washed with water, dried, filtered and evaporated. The crude product was purified by flash chromatography. 0.3 g of the title compound was obtained. Two isomers were obtained in the reaction and separated in later steps. Isomer 1: 1H-NMR (400 MHz, DMSO-d6): δ 1.28 (t, 3H), 2.33 (s, 3H), 4.25 (q, 2H), 4.45-4.58 (m, 2H), 6.23-6.53 (m, 1H), 7.80 (s, 1H). Isomer 2: 1H-NMR (400 MHz, DMSO-d6): δ 1.25 (t, 3H), 2.39 (s, 3H), 4.19 (q, 2H), 4.70-4.83 (m, 2H), 6.18-6.49 (m, 1H), 7.59 (s, 1H).

Provenance & Evidence