2-Vinylpyridine → HCID 66837013, compound

Participants

Reaction Steps

A solution of 2-vinylpyridine (13-1) (2 g, 19.0 mmol) in toluene (40 ml) was treated with ethyl diazoacetate (1.97 ml, 19.0 mmol) and stirred at reflux overnight. The mixture was concentrated in vacuo, and the residue was purified by gradient elution on silica gel (0-50% EtOAc/hexanes) to elute peak 1; the solvent gradient was then ramped to 100% EtOAc to elute peak 2. This yielded the 13-3 (1.6 g, 44%) as the first eluting diastereomer, and the corresponding cis diastereomer 13-2 (914 mg, 25%) as the second eluting diastereomer, both as yellow oils. 1H NMR (500 MHz, CDCl3): δ 8.44 (m, 1H), 7.56 (dt, J=7.6, 1.7 Hz, 1H), 7.22 (dd, J=7.8, 1.0 Hz, 1H), 7.08 (ddd, J=7.6, 4.9, 1.2 Hz, 1H), 4.17 (q, J=7.3 Hz, 2H), 2.58 (ddd, J=10.0, 6.1, 3.9 Hz, 1H), 2.25 (ddd, J=9.5, 5.6, 3.9 Hz, 1H), 1.61, (m, 2H), 1.28 (t, J=7.1 Hz, 3H). LC/MS: m/z (M+H)=192.1.

Provenance & Evidence