Ethyl Glycolate → Ethyl 2-[(6-chloro-3-nitro-2-pyridinyl)oxy]acetate

Participants

Reaction Steps

A stirred solution of 2,6-dichloro-3-nitropyridine (15 g, 78 mmol) and ethyl glycolate (8.1 mL, 86 mmol) in 1,4-dioxane (150 mL) was cooled to 10° C. NaH (60% dispersion in oil) (3.42 g, 86 mmol) was added batchwise. The mixture was then allowed to stir for 6 hours at ambient temperature. The mixture was then cooled (˜10° C.) and treated with saturated aqueous ammonium chloride solution. Water was added until all the solid had dissolved and the mixture was extracted with EtOAc. The EtOAc layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by crystallisation from EtOH (80 mL) to give (6-chloro-3-nitro-pyridin-2-yloxy)-acetic acid ethyl ester (8.55 g). [M+H]+ 261

Provenance & Evidence