Diethyl Ether → 1-(2-Chloropyridin-4-yl)ethan-1-one

To a solution of 2-chloro-4-cyanopyridine (41.6 g) in dry ether under a nitrogen-atmosphere was added methylmagnesium iodide (200 mL, 3M in ether) dropwise. The resulting mixture was stirred at room temperature overnight. The solids which were formed were collected and poured immediately on a mixture of 1000 g ice, 500 mL water and 250 mL 6N HCl. The aqueous solution was allowed to reach room temperature and then extracted with ether (800 mL) and the combined organic layers were dried (sodium sulfate) and evaporated to give a red oil which crystallised on standing. This material was taken up in a mixture of ether (ca 300 mL) and heptane (˜50 mL). The solution was cooled in an acetone/dry-ice bath which resulted in formation of yellow solids that were filtered and air-dried for 30 minutes to give the title compound (21.7 g) as a yellow solid.

1. customThe solids which were formed
2. customwere collected
3. additionpoured immediately on a mixture of 1000 g ice, 500 mL water and 250 mL 6N HCl
4. customto reach room temperature
5. extractionextracted with ether (800 mL)
6. dry with materialthe combined organic layers were dried (sodium sulfate)
7. customevaporated
8. customto give a red oil which
9. customcrystallised
10. additionThis material was taken up in a mixture of ether (ca 300 mL) and heptane (˜50 mL)
11. temperatureThe solution was cooled in an acetone/dry-ice bath which
12. customresulted in formation of yellow solids that
13. filtrationwere filtered
14. customair-dried for 30 minutes

ORD record

ord-017e8675dd984f1aa447e72e881da96b

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952001B2