Neopentyl alcohol → 2,2-Dimethylpropyl 6-chloropyridine-3-carboxylate

To a solution of 10 g (56.8 mmol) of 6-chloropyridine-3-carbonyl chloride in 100 mL of anhydrous toluene are added under argon, at room temperature, 15 g (170.4 mmol) of 2,2-dimethylpropanol. The reaction medium is then heated for 6 hours at 80° C. After cooling to room temperature, the medium is concentrated and the residue obtained is taken up in 800 mL of EtOAc, washed successively with water (2×200 mL), saturated NaHCO3 solution (2×200 mL) and brine (100 mL), dried over Na2SO4, and then concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 5% EtOAc. 11.9 g of 2,2-dimethylpropyl 6-chloropyridine-3-carboxylate are obtained in the form of a white powder.

1. temperatureAfter cooling to room temperature
2. concentrationthe medium is concentrated
3. customthe residue obtained
4. washwashed successively with water (2×200 mL), saturated NaHCO3 solution (2×200 mL) and brine (100 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under reduced pressure
7. custompurified by chromatography on a column of silica gel
8. washeluting with a cyclohexane/EtOAc gradient of 0 to 5% EtOAc

ORD record

ord-095d32159f074af9a6090351ff177e40

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541455B2