Toluene → (2-Chloropyridin-3-yl)methanol

At −78° C., diisobutylaluminum hydride (a 1.0M toluene solution; 4.68 ml) was added dropwise to a methylene chloride (10 ml) solution of ethyl 2-chloronicotinate (347 mg, 1.87 mmol). Thirty minutes later, the reaction mixture was ice cooled, followed by stirring for 15 minutes. After the completion of the reaction was confirmed, brine was added to the reaction mixture and the temperature of the resulting mixture was allowed to rise back to room temperature. The reaction mixture was filtered through Celite. The filtrate was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column and the fraction obtained from the hexane:ethyl acetate (=1:1) eluate was concentrated under reduced pressure, whereby the title compound (211 mg, 79%) was obtained as a white solid.

1. customAt −78° C.
2. customThirty minutes
3. temperaturecooled
4. customto rise back to room temperature
5. filtrationThe reaction mixture was filtered through Celite
6. dry with materialThe filtrate was dried over anhydrous sodium sulfate
7. filtrationAfter filtration
8. concentrationthe filtrate was concentrated under reduced pressure
9. customthe fraction obtained from the hexane
10. concentrationethyl acetate (=1:1) eluate was concentrated under reduced pressure, whereby the title compound (211 mg, 79%)
11. customwas obtained as a white solid

ORD record

ord-a68b47b8dac4441bb3f6b510a1046b92

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07399775B2