2-Methylpyridine → 1-(6-Chloropyridin-2-yl)-2-(pyridin-2-yl)ethyl alcohol

50.2 g of 2-picoline was dissolved in 1363 ml of tetrahydrofuran and 237.2 ml of a 2.5M solution of n-butyllithium in hexane was added to the obtained solution at -50° C. in a nitrogen stream. The obtained mixture was stirred at that temperature for 50 minutes, followed by the addition thereto of a solution of 76.2 g of 6-chloro-2-pyridinecarbaldehyde in 1363 ml of tetrahydrofuran at -50° C. The obtained mixture was stirred at that temperature for 30 minutes and brought to 0° C. at room temperature. Water was added to the resulting mixture to terminate the reaction. Ethyl acetate and water were added to the obtained mixture to conduct extraction. The ethyl acetate phase was washed with a saturated aqueous solution of common salt, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (with a hexane/ethyl acetate (2:1) mixture) to give 38.7 g of the title compound.

1. additionfollowed by the addition
2. customat -50° C
3. stirringThe obtained mixture was stirred at that temperature for 30 minutes
4. custombrought to 0° C. at room temperature
5. customto terminate
6. customthe reaction
7. extractionextraction
8. washThe ethyl acetate phase was washed with a saturated aqueous solution of common salt
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated
11. customThe residue was purified by silica gel chromatography (with a hexane/ethyl acetate (2:1) mixture)

ORD record

ord-83595e1636b1432fbec7b1959a317173

Source dataset

uspto-grants-1996_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05541213