Formaldehyde → 5-Ethyl-2-pyridineethanol

Temperature

-78 °C

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)+.

1. stirringlet stir for 10 min at −78° C
2. customthe cold bath removed
3. stirringstirring
4. waitcontinued for 1 hr
5. customQuenched
6. customreaction with H2O
7. washthe organic layer washed with brine
8. dry with materialdried over MgSO4
9. concentrationconcentrated
10. customThe residue is purified by flash chromatography (silica, 0.5% ammonia/5% methanol/dichloromethane)

ORD record

ord-157b17c9d73a42eda82ea2eb5a4d68f1

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07005440B1