Water → HCID 86755086, compound

HRID 850235Notes

Reaction equation

HRID 850235 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]#[C:10][C:11]#[N:12].[CH2:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)[CH2:14][CH3:15].N1C=CC=CC=1.O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([O:8][C:20]([C:19]2[CH:23]=[CH:24][C:16]([CH2:13][CH2:14][CH3:15])=[CH:17][CH:18]=2)=[O:21])[CH:5]=[CH:4][C:3]=1[C:9]#[C:10][C:11]#[N:12]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 1042934-Propylbenzoyl chlorideHCID 53724298HCID 53724298, compound

Product 1

HCID 86755086HCID 86755086, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 20 mmol of 2-fluoro-4-hydroxyphenylpropiolonitrile and 21 mmol of 4-propylbenzoyl chloride in 50 ml of methylene chloride were added dropwise 25 mmol of pyridine, while stirring under ice-cooling and the solution was stirred for a further 3 hours. Water was added to the reaction solution which was extracted with toluene. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a brown oily product. Purification of the product by a silica gel column chromatography and recrystallization from ethanol gave 8 mmol of the title compound.

Workup

  1. temperaturecooling
  2. stirringthe solution was stirred for a further 3 hours
  3. extractionwas extracted with toluene
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto afford a brown oily product
  8. customPurification of the product
  9. customby a silica gel column chromatography and recrystallization from ethanol

Sources & evidence

ORD record
ord-9c50f92a4cab426db2f64a17b6494362
Source dataset
uspto-grants-2000_01
Patent number
US06017467

Reaction notes

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