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

Temperature

-78 °C

Under stirring at −78° C., t-butyl lithium (a 1.51M pentane solution: 4.6 ml) was added dropwise to an ether (20 ml) solution of 2,5-dichloropyridine (1.02 g, 6.89 mmol). After stirring at −78° C. for 2 hours, pyridine-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 then added to the reaction mixture. The temperature of the resulting mixture was raised to room temperature. The mixture was extracted with methylene chloride. The extract was then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography. The fraction obtained from the methanol:methylene chloride (=1:50) eluate was concentrated under reduced pressure. The solid thus obtained was washed with ether and then collected by filtration to give the title compound (819 mg, 3.21 mmol, 47%) 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 of the resulting mixture was raised to room temperature
4. extractionThe mixture was extracted with methylene chloride
5. dry with materialThe extract was then dried over anhydrous sodium sulfate
6. filtrationAfter filtration
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe residue thus obtained
9. concentrationmethylene chloride (=1:50) eluate was concentrated under reduced pressure
10. customThe solid thus obtained
11. washwas washed with ether
12. filtrationcollected by filtration

ORD record

ord-2f691215afbb4c47bf1848c798865817

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932271B2