Acetonitrile → HCID 58244094, compound

HRID 1242374Notes

Reaction equation

HRID 1242374 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].C([CH2:12][C:13](Br)([CH3:17])[C:14]([O-:16])=[O:15])C.C(=O)([O-])[O-].[K+].[K+].[C:25](#N)[CH3:26]>>[CH2:25]([O:16][C:14](=[O:15])[C:13]([O:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[CH:3]=1)([CH3:12])[CH3:17])[CH3:26]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 22490247Ethyl-bromoisobutyrate

Product 1

HCID 58244094HCID 58244094, compound

Conditions

Temperature
80 °C

Procedure

5.0 g (42.0 mmol) of 3-hydroxybenzonitrile and 16.25 ml=21.29 g (109 mmol) of ethyl-bromoisobutyrate were dissolved in 70 ml acetonitrile; then, 17.40 g (126 mmol) of potassium carbonate were added and the reaction mixture stirred for 16 hours at 80° C. (reflux). It was then cooled down to ambient temperature and the solvent was evaporated. The residue was partitioned between water and ether and extracted twice with ether; the organic phases were washed with water, dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (SiO2, heptane/AcOEt) to finally give 9.10 g of the title compound as colorless oil.

Workup

  1. temperature(reflux)
  2. temperatureIt was then cooled down to ambient temperature
  3. customthe solvent was evaporated
  4. customThe residue was partitioned between water and ether
  5. extractionextracted twice with ether
  6. washthe organic phases were washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe crude product was purified by flash chromatography (SiO2, heptane/AcOEt) to finally give 9.10 g of the title compound as colorless oil

Sources & evidence

ORD record
ord-f84606e22def4c04bea1860f93bcf5df
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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