Water → HCID 23130686, compound

HRID 2080128Notes

Reaction equation

HRID 2080128 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].Br[CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:14][C:13]([CH3:15])=[CH:12][CH2:11][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 700922-Butene, 1-bromo-3-methyl-

Product 1

HCID 23130686HCID 23130686, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxybenzonitrile (1.19 g, 10 mmol) and 4-bromo-2-methyl-2-butene (1.66 g, 10 mmol) were dissolved in N,N-dimethylformamide (5 mL), potassium carbonate (1.66 g, 12 mmol) was added, and the solution was stirred at room temperature for 2 hours. Water (50 mL) was added to the reaction solution, which was then extracted with ethyl acetate (50 mL). The extract was washed, then, dried over anhydrous magnesium sulfate, and the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5), and the title compound (1.71 g, 10 mmol, 99.4%) was obtained as a colorless oil.

Workup

  1. extractionwas then extracted with ethyl acetate (50 mL)
  2. washThe extract was washed
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5)

Sources & evidence

ORD record
ord-af9c19e5bf4a46ea9178c5cdd418cbaf
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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