Potassium Phosphate, Tribasic → Ethyl (2E)-3-(3-cyanophenyl)-2-propenoate

HRID 2184899Notes

Reaction equation

HRID 2184899 reaction equation
FC(F)(F)S(O/[CH:7]=[CH:8]/[C:9]([O:11][CH2:12][CH3:13])=[O:10])(=O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:24]([C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1)#[N:25]>O1CCOCC1>[C:24]([C:26]1[CH:31]=[C:30](/[CH:7]=[CH:8]/[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:29]=[CH:28][CH:27]=1)#[N:25]

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343253-Cyanophenylboronic acidHCID 867581063-[(Trifluoromethylsulfonyl)oxy]acrylic acid ethyl ester

Product 1

HCID 5373498Ethyl (2E)-3-(3-cyanophenyl)-2-propenoateYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl (E)-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-propenoate (390 mg, 1.49 mmol) in 5 ml anhydrous dioxane was added potassium phosphate (474 mg, 2.24 mmol), 3-cyanophenyl boronic acid (217 mg, 1.49 mmol), and tetrakis (triphenylphosphine)palladium(0) (43 mg, 0.038 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 5% EtOAc in hexane as the eluent to give ethyl (E) 3-(3-cyanophenyl)-2-propenoate (240 mg, 71%) as a clear yellow oil after drying. H1NMR (CDCl3): 1.2-1.32 (t, 3H); 2.547 (s, 3H); 4.18-4.24 (m, 2H); 6.113 (s, H); 7.47-7.725 (m, 4H). NOE confirmed stereo orientation.

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 5% EtOAc in hexane as the eluent

Sources & evidence

ORD record
ord-fb42fb351bcb4c479abd111a9d69c398
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

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