Diethyl Oxalate → HCID 86619018, compound

To a heterogeneous solution of potassium ethoxide (6.56 g, 77.9 mmol) in diethyl ether (55 mL), was slowly added diethyl oxalate (10.6 mL, 77.9 mmol). A slight exotherm resulted. After stirring 5 min, a homogeneous yellow solution resulted, but after 10 min, a heterogeneous yellow slurry was observed. Addition of 2-chloro-4-methyl-3-nitropyridine (13.45 g, 77.9 mmol) as a solid, with a diethyl ether rinse (23 mL), resulted in a dark violet solution with a dark precipitate. The mixture was stirred at room temperature overnight (21 h). The solid precipitate was filtered, rinsed thoroughly with diethyl ether, and air-dried to give potassium (1Z)-1-(2-chloro-3-nitropyridin-4-yl)-3-ethoxy-3-oxoprop-1-en-2-olate (19.8 g, 63.6 mmol, yield 81%) as an orange solid. The crude product was used directly without further purification or identification.

1. customA slight exotherm resulted
2. customa homogeneous yellow solution resulted
3. waitafter 10 min
4. washwith a diethyl ether rinse (23 mL)
5. customresulted in a dark violet solution with a dark precipitate
6. stirringThe mixture was stirred at room temperature overnight (21 h)
7. filtrationThe solid precipitate was filtered
8. washrinsed thoroughly with diethyl ether
9. customair-dried

ORD record

ord-b9ac46418dce47f389fdb4613caa8cdd

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07608627B2