Water → HCID 58387595, compound

Temperature

-50 °C

An oven dried 250 mL 3 neck r.b.f. equipped with an internal thermometer was charged with diethyl ether (180 mL) and titanium tetrachloride, 1.0 M in dichloromethane (20.5 mL, 20.5 mmoles) under an Argon atmosphere. The solution was cooled in a CO2(a)/acetone −78° C. bath and methyl lithium, 1.6 M in diethyl ether (12.8 mL, 20.5 mmoles) was added via a syringe at a rate such that the internal temperature was </=−50° C. The resultant anion solution was stirred at −50° C. for 1 hour, at which time 2-chloro-5-nitroisonicotinaldehyde (2.54 g, 13.66 mmoles) in diethyl ether (16+4 mL) was added via syringe with the internal temp </=−50° C. After stirring for an additional hour at −50° C., the reaction was poured into H2O (500 mL), and after mixing two light yellow layers formed. Diethyl ether was added (500 mL), the layers were separated, and the organic was washed with H2O (250 mL), with NaCl(sat.) (250 mL), dried over MgSO4, filtered and concentrated yielding 1-(2-chloro-5-nitropyridin-4-yl)ethanol (2.76 g, 100% yield). LCMS (m/z): 203.0 (MH+); LC Rt=2.42 min. 1H NMR (CDCl3): δ 8.99 (s, 1H), 7.88 (s, 1H), 5.52 (m, 1H), 1.56 (d, J=9.0, 3H).

1. dry with materialAn oven dried 250 mL 3 neck r.b.f
2. customequipped with an internal thermometer
3. additionwas added via a syringe at a rate such that the internal temperature
4. custom</=−50° C
5. additionwas added via syringe with the internal temp </=−50° C
6. additionafter mixing two light yellow layers
7. customformed
8. customthe layers were separated
9. washthe organic was washed with H2O (250 mL), with NaCl(sat.) (250 mL)
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-806405ba57444fdc8f75b181f0149724

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735424B2