Ethyl diazoacetate → HCID 86732054, compound

Participants

Reaction Steps

To a solution of 4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methyl-6-vinylpyridine (24-4, 620 mg, 2.69 mmol) in toluene (12 mL) was added at reflux a solution of ethyl diazoacetate (614 mg, 5.38 mmol) in toluene (2 mL) in three portions over 10 minutes. The reaction mixture was refluxed for 2 hours, cooled to room temperature, and concentrated. The residue was purified by silica gel column chromatography (0-90% ethyl acetate in hexanes) to afford ethyl trans-2-(4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-methylpyridin-2-yl)cyclopropanecarboxylate (24-5) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.17 (d, 1H, J=1.7 Hz), 7.09 (d, 1H, J=1.7 Hz), 4.17 (q, 2H, J=7.2 Hz), 2.63-2.57 (m, 1H), 2.59 (s, 3H), 2.52 (s, 3H), 2.41 (s, 3H), 2.33-2.27 (m, 1H), 1.70-1.57 (m, 2H), 1.28 (d, 3H, J=7.2 Hz). LRMS m/z (M+H) 301 found, 301 required.

Provenance & Evidence