Cesium carbonate → HCID 117874690, compound

HRID 715919Notes

Reaction equation

HRID 715919 reaction equation
Cl[C:2]([F:7])([F:6])C([O-])=O.[Na+].[CH3:9][CH:10]([OH:13])[C:11]#[CH:12].[N-:14]=[N+:15]=[N-:16].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C.S([O-])([O-])(=O)=O.[Cu+2].[Cu].O.C(O)(C)(C)C>[F:7][CH:2]([F:6])[N:14]1[CH:12]=[C:11]([CH:10]([OH:13])[CH3:9])[N:16]=[N:15]1

Participants

10

Reactant 4

HCID 10796Cesium carbonateHCID 162393-Butyn-2-olHCID 33557Sodium AzideHCID 2734985Sodium chlorodifluoroacetate

Product 1

HCID 117874690HCID 117874690, compound

Reagents, catalysts & solvents 5

HCID 23978CopperCatalystHCID 24462Copper SulfateCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tert-butanol (17.4 ml), water (17.4 ml), and a 1 M aqueous copper(II) sulfate solution (4.64 ml) were added to sodium chlorodifluoroacetate (3.54 g), but-3-yn-2-ol (2.00 ml), sodium azide (1.66 g), cesium carbonate (11.3 g), and copper (1.18 g), and the mixture was reacted for 30 minutes using a microwave reaction apparatus (300 W, 125° C.). The reaction solution was diluted with ethyl acetate. While being washed, the dilution was filtered to remove the aqueous layer. The organic layer was dried over anhydrous sodium sulfate and then filtered. The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane-methyl acetate) to obtain the title compound (196 mg).

Workup

  1. customthe mixture was reacted for 30 minutes
  2. customa microwave reaction apparatus (300 W, 125° C.)
  3. washWhile being washed
  4. filtrationthe dilution was filtered
  5. customto remove the aqueous layer
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (n-hexane-methyl acetate)

Sources & evidence

ORD record
ord-d47f7bbf97e446fbbc867006314bbcf4
Source dataset
uspto-grants-2015_11
Patent number
US09187489B2

Reaction notes

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