Oxalyl chloride → HCID 54490493, compound

HRID 1409544Notes

Reaction equation

HRID 1409544 reaction equation
[C:1]([C:3](=[C:8](C(OC(F)(F)F)=O)[C:9]([F:12])([F:11])[F:10])[C:4]([O:6][CH3:7])=[O:5])#[N:2].C(Cl)(=O)C([Cl:23])=O>C(Cl)Cl.N1C=CC=CC=1.O>[Cl:23][C:8]([C:9]([F:12])([F:11])[F:10])=[C:3]([C:1]#[N:2])[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 2

HCID 65578Oxalyl chlorideHCID 86628631HCID 86628631, compound

Product 1

HCID 54490493HCID 54490493, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of the compound 2a and 2b obtained in the above step (1) (27.6 g) in methylene chloride (200 mL) were gradually added dropwise oxalyl chloride (31.6 mL) and a few drops of pyridine, and the mixture was refluxed under heating for 4 hours. The reaction mixture was gradually poured in water, and the mixture was extracted with methylene chloride. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to give methyl 3-chloro-2-cyano-4,4,4-trifluoro-2-butenoate as a crude product.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 4 hours
  3. extractionthe mixture was extracted with methylene chloride
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ee549f59a7ed4e818532adf39899feee
Source dataset
uspto-grants-2014_12
Patent number
US08921380B2

Reaction notes

Loading…