Hydrochloric Acid → alpha-2-Pyridylpyridine-2-methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 80 mL n-BuLi in hexanes (2.5 M, 0.2 mol) was added 2-pyridylbromide (31.6 gram 0.2 mol) in 100 mL of ether at −80° C.-−60° C. The suspension was stirred for 1 h, and the temperature was allowed to rise to −45° C. Subsequently 2-pyridinecarboxaldehyde (21.42 gram 0.2 mol) in of ether (100 mL) was added during 30 min. To the thick slurry was added additional THF (200 mL) and the mixture was stirred for 1.5 h at −40° C.-−30° C. and then the mixture was allowed to warm up to −10° C. The mixture was poured into water (200 ml) and acidified with 2 M HCl to pH=1-2 and the layers were separated. The aqueous layer was extracted twice with ether (100 mL) and neutralized with saturated Na2CO3(aq) to pH=8. The aqueous layer was extracted CH2Cl2 (3×100 ml). Drying (Na2SO4) and evaporation of the solvent yielded a brown oil. Vacuum distillation (118° C., 0.2 mmHg) afforded di(2-pyridinyl)methanol (19.42 gram, 104.4 mmol, 52%) as a yellow oil. 1H-NMR (200 MHz. CDCl3) δ 5.88 (s, 2H), 7.11-7.19 (m, 2H), 7.47-7.67 (m, 4H). 8.50-8.54 (m, 2H). 13C-NMR (50.3 MHz, CDCl3) δ 75.0 (d), 121.0 (d), 122.5 (d), 136.8 (d), 1448.1 (d), 160.7 (s).

Provenance & Evidence