Formaldehyde → 5-Ethyl-2-pyridineethanol

Participants

Reaction Conditions

Reaction Steps

To a cooled solution (−10° C.) of diisopropylamine (2.31 mL, 16.5 mL) in THF (45 mL) is added dropwise (2.5M) n-butyllithium (6.6 mL, 16.5 mmol), let stir 10 min. then cooled to −78° C. To this mixture is added dropwise a solution of 5-ethyl-2-methylpyridine (1.98 mL, 15 mmol) in THF (3 mL) and let stir for 10 min at −78° C. To the reaction mixture is added paraformaldehyde (1.13 g, 37.5 mmol), the cold bath removed and stirring continued for 1 hr. Quenched reaction with H2O, diluted with EtOAc and the organic layer washed with brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (silica, 0.5% ammonia/5% methanol/dichloromethane) to give the title compound as a pale yellow oil. MS (EI) 151 (M)+.

Provenance & Evidence