Hydrochloric Acid → 2-(6-Chloropyridin-2-yl)ethanol

To a solution of ethyl (6-chloro-2-pyridinyl)acetate (Example 469, 5.00 g, 25 mmol) in THF (50 mL) was added LiBH4 (13.0 mL, 25.0 mmol, 2M solution in THF) at 0° C. The mixture was stirred at rt for 18 h, then water was slowly added [strong gaseous evolution] followed by HCl (10 mL, 1N aqueous solution). The mixture was extracted with CH2Cl2. The combined organic phases were dried (Na2SO4), filtered and then concentrated under reduced pressure. The residue was purified using a short pad of silica gel (4:1 hexanes/EtOAc) to give the product (3.00 g, 76%) as a light-yellow oil which solidified upon standing. 1H NMR (400 MHz, CDCl3) δ 2.97 (t, 2H), 3.98 (t, 2H), 7.10 (dd, 2H), 7.54 (t, 1H).

1. extractionThe mixture was extracted with CH2Cl2
2. dry with materialThe combined organic phases were dried (Na2SO4)
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified

ORD record

ord-f5e4a07b74a1474abf3b30846180c1bc

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07906653B2