Methyl Ethyl Ketone → HCID 178468923, compound

To a solution of diethyl ethanedioate (45.2 g) in absolute ethanol (140 ml) cooled in an ice/industrial methylated spirit bath was added ethanolic sodium ethoxide (100 ml; 21% w/w) dropwise, keeping the temperature below 3° C. and the mixture stirred for 15 min in an ice bath. 2-Butanone (22.1 g) was added and the mixture stirred in an ice bath for 15 min before being allowed to warm to RT overnight. The mixture was stirred at 40° C. for 6 h and then cooled to 0° C. Glacial acetic acid (17.5 ml) was added dropwise, maintaining the temperature below 3° C. The resultant precipitate was broken up and ethanol (100 ml) added to enable the mixture to stir. Hydrazine hydrate (14 ml) was added dropwise, maintaining the temperature below 7° C. The mixture was stirred in the cold bath for 10 min and then allowed to warm to RT overnight. The solvent was removed in vacuo and the residue partitioned between DCM (300 ml) and water (100 ml). The organic phase was washed with water (2×100 ml), dried over magnesium sulphate and the solvent removed to give the title compound (41.3 g) as a red oil.

1. customthe temperature below 3° C.
2. stirringthe mixture stirred in an ice bath for 15 min
3. stirringThe mixture was stirred at 40° C. for 6 h
4. temperaturecooled to 0° C
5. temperaturemaintaining the temperature below 3° C
6. additionadded
7. stirringto stir
8. temperaturemaintaining the temperature below 7° C
9. stirringThe mixture was stirred in the cold bath for 10 min
10. temperatureto warm to RT overnight
11. customThe solvent was removed in vacuo
12. customthe residue partitioned between DCM (300 ml) and water (100 ml)
13. washThe organic phase was washed with water (2×100 ml)
14. dry with materialdried over magnesium sulphate
15. customthe solvent removed

ORD record

ord-6fadb195428b4c7cb109489293fcf129

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658635B2