1,4-Dioxane → HCID 86758117, compound

HRID 2184914Notes

Reaction equation

HRID 2184914 reaction equation
[CH3:1][O:2][CH2:3]/[C:4](/OS(C(F)(F)F)(=O)=O)=[CH:5]/[C:6]([O:8][CH3:9])=[O:7].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:26]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)#[N:27].O1CCOC[CH2:38]1>>[C:26]([C:28]1[CH:29]=[C:30](/[C:4](/[CH2:3][O:2][CH2:1][CH3:38])=[CH:5]\[C:6]([O:8][CH3:9])=[O:7])[CH:31]=[CH:32][CH:33]=1)#[N:27]

Participants

5

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 27343253-Cyanophenylboronic acidHCID 86758116HCID 86758116, compound

Product 1

HCID 86758117HCID 86758117, compoundYield 75%

Procedure

To a solution of methyl (Z)-4-methoxy-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-butenoate (246 mg, 1.0 mmol) in 5 ml anhydrous dioxane was added potassium phosphate (318 mg, 1.5 mmol), 3-cyanophenyl boronic acid (162 mg, 1.0 mmol), and tetrakis (triphenylphosphine)palladium(0) (29 mg, 0.0251 mmol). Reaction mixture was heated to reflux and stirred overnight. Mixture was filtered through a pad of Celite, diluted with 20 ml ethyl acetate. Organic was washed with 2×20 ml water, 2×20 ml saturated brine solution, dried over magnesium sulfate, filtered and concentrated in vacuo to give methyl (E)-3-(3-cyanophenyl)-4-ethoxy-2-butenoate (220 mg, 75%) as a clear brown oil which was sufficiently pure to be used without further purification. ES-MS (M+H+): 232.1

Workup

  1. customReaction mixture
  2. temperaturewas heated
  3. temperatureto reflux
  4. filtrationMixture was filtered through a pad of Celite
  5. additiondiluted with 20 ml ethyl acetate
  6. washOrganic was washed with 2×20 ml water, 2×20 ml saturated brine solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d512a9706844510a67bc114e063127e
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

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