Acetaldehyde → 1-(5-(Methoxymethoxy)-2-neopentylpyridin-4-yl)ethanol

Temperature

-78 °C

To a solution of 5-(methoxymethoxy)-2-neopentylpyridine (16.5 g, 79 mmol) and in THF (200 mL)-78° C. is added tert-butyllithium (46 ml, 79 mmol) (1.7 M in pentane) over 2 min via cannula. The reaction was stirred at −78° C. 30 min, and acetaldehyde (11 ml, 197 mmol) was added. The reaction was stirred at −78° C. 10 min, then the reaction was warmed to rt and stirred 3 h. The reaction was quenched by addition of saturated aqueous NH4Cl (400 mL), extracted with EtOAc (3×200 mL), the combined organic layers washed with saturated NaCl (10 mL), dried (Na2SO4), and concentrated to give a orange oil, which was purified by chromatography on an ISCO (330 g SiO2, 10%-50% EtOAc/Hexane) gives 1-(5-(methoxymethoxy)-2-neopentylpyridin-4-yl)ethanol as a clear, light yellow oil.

1. stirringThe reaction was stirred at −78° C
2. temperature10 min, then the reaction was warmed to rt
3. stirringstirred 3 h
4. customThe reaction was quenched by addition of saturated aqueous NH4Cl (400 mL)
5. extractionextracted with EtOAc (3×200 mL)
6. washthe combined organic layers washed with saturated NaCl (10 mL)
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated
9. customto give a orange oil, which
10. customwas purified by chromatography on an ISCO (330 g SiO2, 10%-50% EtOAc/Hexane)

ORD record

ord-f93c7ffa32d04f51b69264def1aed3df

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633315B2