Ethyl diazoacetate → HCID 86732060, compound

Participants

Reaction Steps

To a solution of 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-methyl-4-vinylpyridine (25-1) (200 mg, 0.933 mmol) in toluene (8 mL) was added at reflux ethyl diazoacetate (852 mg, 7.47 mmol) in three portions over 4 hours. The mixture was refluxed for another 2 hours, cooled to room temperature, and concentrated. The residue was purified by silica gel column chromatography (0-70% ethyl acetate in hexanes) to give ethyl trans-2-(2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-methylpyridin-4-yl)cyclopropanecarboxylate (25-2) as a yellow oil. 1H NMR (300 MHz, CDCl3) 57.32 (br s, 1H), 6.83 (br s, 1H), 4.18 (q, 2H, J=7.2 Hz), 2.80 (s, 3H), 2.55-2.46 (m, 1H), 2.51 (s, 3H), 2.41 (s, 3H), 2.09-1.99 (m, 1H), 1.73-1.63 (m, 1H), 1.46-1.36 (m, 1H), 1.28 (t, 1H, J=7.2 Hz). LRMS m/z (M+H) 301 found, 301 required.

Provenance & Evidence