Hydrochloric Acid → HCID 23103646, compound

Temperature

0 °C

A 1.58 M n-hexane solution of n-butyllithium (19.0 mL, 0.0300 mol) and THF (50 mL) were mixed, followed by addition of 2,2,6,6-tetramethylpiperidine (4.2 g, 0.0300 mol) at −78° C. The reaction mixture was warmed to 0° C. and stirred for 20 minutes. After the reaction mixture was cooled again to −78° C., a solution of 2-chloropyrazine (2.5 g, 0.0218 mol) in THF (5 mL) was added dropwise thereto and stirred at −78° C. for 1 hour. A solution of 4-ethylbenzaldehyde (3.3 g, 0.0240 mol) in THF (5 mL) was added dropwise to the reaction mixture, followed by stirring for 30 minutes. Concentrated hydrochloric acid (10 mL) and ethanol (5 mL) were added to the reaction mixture. After warming to room temperature, the reaction mixture was poured into saturated aqueous sodium bicarbonate and the resulting mixture was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2) to give (2-chloropyrazin-3-yl)-(4-ethylphenyl)methanol (3.1 g, 57%) as a brown oil.

1. temperatureAfter the reaction mixture was cooled again to −78° C.
2. stirringstirred at −78° C. for 1 hour
3. stirringby stirring for 30 minutes
4. temperatureAfter warming to room temperature
5. extractionthe resulting mixture was extracted twice with ethyl acetate
6. washThe combined organic layers were washed with saturated aqueous sodium chloride
7. dry with materialdried over anhydrous magnesium sulfate
8. distillationAfter the solvent was distilled off under reduced pressure
9. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2)

ORD record

ord-e800445d58c149ac9c6dd3cc0bc88abe

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07439232B2