Acetic Acid → HCID 178468923, compound

Ethanolic sodium ethoxide solution (21% w/w; 143 ml, 0.39 mol) was added dropwise to a stirred, ice-cooled solution of diethyl oxalate (59.8 ml, 0.44 mol) in absolute ethanol (200 ml) under an atmosphere of nitrogen and stirred for 15 minutes. Butan-2-one (39 ml, 0.44 mol) was added dropwise and the reaction mixture stirred for 18 hours warming to room temperature and then for 6 hours at 40° C. The resultant mixture was cooled to 0° C., glacial acetic acid (25 ml, 0.44 mol) was added dropwise and stirred for 30 minutes at 0° C. Hydrazine hydrate (20 ml, 0.44 mol) was added dropwise and the reaction mixture was allowed to warm to room temperature and stirred for 18 hours. The solvent was removed under reduced pressure and ,the residue was partitioned between dichloromethane (300 ml) and water (100 ml). The organic layer was separated and washed with water (2×100 ml), dried over Na2SO4 and concentrated under reduced pressure to give the title compound (66.0 g).

1. stirringthe reaction mixture stirred for 18 hours
2. waitfor 6 hours at 40° C
3. stirringstirred for 30 minutes at 0° C
4. temperatureto warm to room temperature
5. stirringstirred for 18 hours
6. customThe solvent was removed under reduced pressure and ,the residue
7. customwas partitioned between dichloromethane (300 ml) and water (100 ml)
8. customThe organic layer was separated
9. washwashed with water (2×100 ml)
10. dry with materialdried over Na2SO4
11. concentrationconcentrated under reduced pressure

ORD record

ord-c014ad5d867f4ae2b9e31815f67dd510

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06670366B1