Potassium Phosphate, Tribasic → HCID 22458359, compound

HRID 2184923Notes

Reaction equation

HRID 2184923 reaction equation
FC(F)(F)S(O[C:7]1[CH2:11][CH2:10][CH2:9][C:8]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:27]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)#[N:28]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:27]([C:29]1[CH:34]=[C:33]([C:7]2[CH2:11][CH2:10][CH2:9][C:8]=2[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:32]=[CH:31][CH:30]=1)#[N:28]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343253-Cyanophenylboronic acidHCID 2779887Ethyl 2-[(trifluoromethanesulfonyl)oxy]cyclopent-1-ene-1-carboxylate

Product 1

HCID 22458359HCID 22458359, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 2-{[(trifluoromethyl)sulfonyl]oxy}-1-cyclopentene-1-carboxylate (1.2 g, 4.16 mmol) in 10 ml anhydrous dioxane was added potassium phosphate (1.32 g, 6.2 mmol), 3-cyanophenyl boronic acid (0.612 g, 4.16 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.10 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 2-(3-cyanophenyl)-1-cyclopentene-1-carboxylate (0.7 g, 71%) as a light yellow oil after drying. ES-MS (M+H+): 242.15. H1NMR (CDCl3) δ: 1.09-1.13 (t, 3H); 1.96-2.01 (m, 2H); 2.80-2.84 (m, 4H); 7.39-7.59 (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 5% EtOAc in hexane as the eluent

Sources & evidence

ORD record
ord-87ce1722709542409b02820f1aa3d8a4
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

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