Potassium Phosphate, Tribasic → HCID 86758109, compound

HRID 2184905Notes

Reaction equation

HRID 2184905 reaction equation
[F:1][C:2]([F:19])([F:18])/[C:3](/OS(C(F)(F)F)(=O)=O)=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:28]([C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1)#[N:29]>O1CCOCC1>[C:28]([C:30]1[CH:35]=[C:34](/[C:3](/[C:2]([F:19])([F:18])[F:1])=[CH:4]\[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:33]=[CH:32][CH:31]=1)#[N:29]

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343253-Cyanophenylboronic acidHCID 10860029HCID 10860029, compound

Product 1

HCID 86758109HCID 86758109, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl (Z)-4,4,4-trifluoro-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-butenoate (250 mg, 0.79 mmol) in 5 ml anhydrous dioxane was added potassium phosphate (251 mg, 1.19 mmol), 3-cyanophenyl boronic acid (116 mg, 0.79 mmol), and tetrakis (triphenylphosphine)palladium(0) (23 mg, 0.02 mmol). Reaction mixture was heated to reflux and stirred overnight. Mixture was filtered through a pad of Celite, diluted with 50 ml ethyl acetate, washed with 2×50 ml water, 2×50 ml saturated brine solution, dried over magnesium sulfate, filtered and concentrated in vacuo. Residue was chromatographed on silica gel using 20% EtOAc in hexane as the eluent to give ethyl (2E)-3-(3-cyanophenyl)-4,4,4-trifluorobut-2-enoate (150 mg, 79%) as a yellow residue after drying. H1NMR (CDCl3) 1.107-1.142 (t, 3H); 4.04-4.107 (m, 2H); 6.684 (s, H); 7.38-7.72 (m, 4H).

Workup

  1. customReaction mixture
  2. temperaturewas heated
  3. temperatureto reflux
  4. filtrationMixture was filtered through a pad of Celite
  5. additiondiluted with 50 ml ethyl acetate
  6. washwashed with 2×50 ml water, 2×50 ml saturated brine solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customResidue was chromatographed on silica gel using 20% EtOAc in hexane as the eluent

Sources & evidence

ORD record
ord-933de25237ca404d957ea82f432af56b
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

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