Ammonium Chloride → HCID 59754786, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (−15° C.) solution of anhydrous EtOH (270 mL) was added sodium metal (4.46 g, 0.194 mol) slowly. After complete reaction a mixture of 3-formyl-5-methoxypyridine (7.5 g, 54.7 mmol) and ethylazidoacetate (25.0 g, 0.194 mol) was added so as to maintain an internal temperature of −15° C. The reaction mixture was kept at −15° C. for 72 hours after which it was poured into a 30% aq. NH4Cl solution, extracted with EtOAc (2×250 mL), the organic phase dried (MgSO4), filtered and evaporated in vacuo. The residue was purified on silica gel eluting with a gradient of 0 to 35% EtOAc in hexanes to afford the title compound.

Provenance & Evidence