Acetonitrile → HCID 57526929, compound

HRID 1452665Notes

Reaction equation

HRID 1452665 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[C:10]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:11][CH2:12][CH:13]=[CH2:14].C(N(CC)CC)C.CC#N>C1COCC1>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1/[CH:14]=[CH:13]/[CH2:12][CH2:11][C:10]([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 68257o-IodoanisoleHCID 74786Ethyl 4-pentenoate

Product 1

HCID 57526929HCID 57526929, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 200-mL RB-flask was added 2-iodoanisole (5.00 g, 21.4 mmol), ethyl 4-pentenoate (3.30 g, 25.6 mmol), tetrakis(triphenyl phosphine)palladium(0) (0.740 g, 0.600 mmol), triethylamine (6.00 mL, 42.7 mmol) and a mixture of CH3CN (45.0 mL) and THF (15.0 mL). The reaction mixture was refluxed for overnight and then cooled to room temperature. After solvents were removed in vacuo, the resulted dark brown residue was dissolved in 5% HCl (aq) and extracted with CH2Cl2 three times. The combined extracts were washed by saturated NaHCO3 solution, dried over MgSO4, concentrated in vacuo. The dark brown oil was purified by chromatography (silica gel, EtOAc/Hexanes 1:10) to afford the product as light yellow oil (3.40 g, 68%).

Workup

  1. temperatureThe reaction mixture was refluxed for overnight
  2. customAfter solvents were removed in vacuo
  3. dissolutionthe resulted dark brown residue was dissolved in 5% HCl (aq)
  4. extractionextracted with CH2Cl2 three times
  5. washThe combined extracts were washed by saturated NaHCO3 solution
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe dark brown oil was purified by chromatography (silica gel, EtOAc/Hexanes 1:10)

Sources & evidence

ORD record
ord-a087c93388254ed1a53e5496f2f7b737
Source dataset
uspto-grants-2009_01
Patent number
US07473698B2

Reaction notes

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