Tetrahydrofuran → HCID 86678964, compound

Participants

Reaction Conditions

Reaction Steps

Isopropylmagnesium chloride LiCl complex (1627 μl, 2.115 mmol, 1.3 M in THF) was added to a THF solution of 4-iodo pyrazole (400 mg, 1.923 mmol) cooled to −30° C. The reaction was stirred for hours with the temperature maintained between −20 and −30° C. After two hours, ethyl 3,3-dicyano-2-methylprop-2-enoate (1442 μl, 1.442 mmol, 1 M solution in benzene) was quickly added and the reaction was warmed to room temperature and stirred for five minutes. The reaction was then quenched with saturated aqueous NH4Cl and extracted between EtOAc. The organic layer was dried (sodium sulfate) and concentrated in vacuo. Purification by silica gel column chromatography using a hexanes/EtOAc gradient afforded the title product as a clear oil, 1H NMR (500 MHz, CHCl3-d): δ 7.44 (s, 1H); 7.42 (s, 1H); 4.44 (s, 1H); 4.28-4.19 (m, 2H); 3.86 (s, 3H); 1.84 (s, 3H); 1.25 (t, J=7.12 Hz, 3H).

Provenance & Evidence