Potassium Phosphate, Tribasic → HCID 86758114, compound

HRID 2184912Notes

Reaction equation

HRID 2184912 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[C:6](/OS(C(F)(F)F)(=O)=O)=[CH:7]/[C:8]([O:10][CH2:11][CH3:12])=[O:9].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:29]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)#[N:30]>O1CCOCC1>[C:29]([C:31]1[CH:36]=[C:35](/[C:6](/[C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:7]\[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:34]=[CH:33][CH:32]=1)#[N:30]

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343253-Cyanophenylboronic acidHCID 86758115HCID 86758115, compound

Product 1

HCID 86758114HCID 86758114, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl (Z)-3-(2-furyl)-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-propenoate (500 mg, 1.59 mmol) in 7 ml anhydrous dioxane was added potassium phosphate (506 mg, 2.4 mmol), 3-cyanophenyl boronic acid (234 mg, 1.59 mmol), and tetrakis (triphenylphosphine)palladium(0) (46 mg, 0.04 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. The crude residue was chromatographed on silica gel using a gradient from 5% EtOAc in hexane to 10% EtOAc in hexane as the eluent to give ethyl (E) 3-(3-cyanophenyl)-3-(2-furyl)-2-propenoate (100 mg, 24%) as a clear yellow oil after drying. H1NMR (CDCl3) 1.1-1.14 (t, 3H); 4.016-4.035 (m, 2H); 5.293 (s, H); 7.45-7.549 (m, 3H); 7.669 (m, H). ES-MS (M+H+): 268.05

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. customThe crude residue was chromatographed on silica gel using a gradient from 5% EtOAc in hexane to 10% EtOAc in hexane as the eluent

Sources & evidence

ORD record
ord-2fe3b3383a394432804f03b110599a3a
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

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