Water → (3,6-Dichloropyridin-2-yl) (pyridine-4-yl)methanol

Temperature

-78 °C

Under stirring at −78° C., tert-butyl lithium (1.51M pentane solution: 4.6 ml) was added dropwise to a solution of 2,5-dichloropyridine (1.02 g, 6.89 mmol) in ether (20 ml). After stirring at −78° C. for 2 hours, pyridin-4-carbaldehyde (0.65 ml, 6.89 mmol) was added to the reaction mixture. The resulting mixture was stirred at −78° C. for 1 hour. Water was added to the reaction mixture and the temperature was raised to room temperature. The mixture was extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate and filtered. The filtrate was then concentrated under reduced pressure. The residue thus obtained was subjected to chromatography on a silica gel column. A fraction obtained from the eluate with methanol:methylene chloride (1:50) was concentrated under reduced pressure. The solid thus obtained was washed with ether and collected by filtration, whereby the title compound (819 mg, 3.21 mmol, 47%) was obtained as a white powder.

1. stirringAfter stirring at −78° C. for 2 hours
2. stirringThe resulting mixture was stirred at −78° C. for 1 hour
3. temperaturethe temperature was raised to room temperature
4. extractionThe mixture was extracted with methylene chloride
5. dry with materialThe extract was dried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was then concentrated under reduced pressure
8. customThe residue thus obtained
9. concentrationwas concentrated under reduced pressure
10. customThe solid thus obtained
11. washwas washed with ether

ORD record

ord-b79583c4ea4f4da8830594ad67b8bf8b

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07399775B2