Hydrochloric Acid → 2-(6-Chloropyridazin-3-yl)propan-2-ol

Temperature

-20 °C

To a solution of MeTHF (2.5 mL) and toluene (10 mL) was added MeMgCl (3.0 M, 9.7 mL) and stirred at −20° C. under N2 atmosphere followed by the addition of t-BuOH (0.5 mL, 5.79 mmol) in MeTHF (7 mL) dropwise. The solution was allowed to stir for 30 min and warmed to 3° C. and cooled backed down to −20° C. followed by the addition of the methyl 6-chloropyridazine-3-carboxylate (1.0 g, 5.79 mmol) in portions. The solution quickly turned dark violet and stirred at 0° C. for 30 min. The solution was then poured into a flask containing 1 N HCl at −5° C. and diluted with EtOAc followed by stirring for 10 min. The layers were separated and the organic layers were washed with sat. NaHCO3 and brine. The acidic aqueous layer was neutralized with sat. NaHCO3 and extracted with EtOAc. The organic layers were combined and concentrated under rotary evaporation. Column chromatography Hex to 100% EtOAc provided the title compound.

1. stirringto stir for 30 min
2. temperaturewarmed to 3° C.
3. temperaturecooled
4. custombacked down to −20° C.
5. stirringThe solution quickly turned dark violet and stirred at 0° C. for 30 min
6. additionThe solution was then poured into a flask
7. stirringby stirring for 10 min
8. customThe layers were separated
9. washthe organic layers were washed with sat. NaHCO3 and brine
10. extractionextracted with EtOAc
11. concentrationconcentrated under rotary evaporation

ORD record

ord-77a64959dc8a463b85cd2e3b44b42f33

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367706B2