Hydrochloric Acid → HCID 22009545, compound

HRID 322036Notes

Reaction equation

HRID 322036 reaction equation
C[C:2]([CH3:16])([O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:9]#[N:10])[C:3]#[CH:4].[F-].[Cs+].Cl.[CH2:20](N(CC)C1C=CC=CC=1)C>>[CH3:15][O:14][C:13]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]2[C:6]=1[O:5][C:2]([CH:3]([CH3:4])[CH3:20])=[CH:16]2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7061N,N-DiethylanilineHCID 25953Cesium fluorideHCID 22009522HCID 22009522, compound

Product 1

HCID 22009545HCID 22009545, compound

Procedure

5.3 g of 3-(1,1-dimethylprop-2-yn-1-yloxy)-4-methoxybenzonitrile and 5.3 g of cesium fluoride are refluxed for 12 h in 30 ml of N,N-diethylaniline with nitrogen aeration. After cooling, the mixture is stirred into 300 ml of 4 N hydrochloric acid, the resulting emulsion is extracted three times with 5.0 ml of ethyl acetate, and the organic extracts are combined, dried over calcined potassium carbonate and evaporated in vacuo. The residue is chromatographed on silica gel using toluene. After evaporating the corresponding fractions, the title compound is obtained as an oil.

Workup

  1. temperatureAfter cooling
  2. extractionthe resulting emulsion is extracted three times with 5.0 ml of ethyl acetate
  3. customdried
  4. customevaporated in vacuo
  5. customThe residue is chromatographed on silica gel
  6. customAfter evaporating the corresponding fractions

Sources & evidence

ORD record
ord-e6d1187072c34116a9f0d90ee748b37c
Source dataset
uspto-grants-2001_04
Patent number
US06211203B1

Reaction notes

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