Acetone Cyanohydrin → HCID 14406046, compound

HRID 2291221Notes

Reaction equation

HRID 2291221 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH:21]1[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][C:22]1=[O:28].C(N(CC)CC)C.CC(C)(O)C#N>C(Cl)Cl.CCOCC>[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH:21]1[CH2:26][CH2:25][C:24](=[O:27])[CH:23]([C:5](=[O:6])[C:4]2[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=2[C:2]([F:13])([F:12])[F:1])[C:22]1=[O:28]

Participants

7

Reactant 4

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 14406045HCID 14406045, compound

Product 1

HCID 14406046HCID 14406046, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

2-Trifluoromethylbenzoyl chloride (7.1 g, 0.034 mole) and 4-(2-fluorophenyl)-1,3-cyclohexanedione (7.0 g, 0.034 mole) were dissolved in methylene chloride. Triethylamine (4.1 g, 0.041 mole) was added dropwise and the resulting solution stirred for one hour. The solution was washed with 2 normal hydrochloric acid (2N HCl), 5% potassium carbonate solution, and saturated sodium chloride solution, dried over anhydrous magnesium sulfate (MgSO4) and concentrated under vacuum. The residue was dissolved in 40 ml of acetonitrile. Triethylamine (1 equivalent) and acetone cyanohydrin (0.4 ml) were added and the solution stirred for 1 hour at room temperature. After dilution with ether (150 ml), the solution was washed with 2N HCl. The ether layer was then stirred with 100 ml of 5% copper (II) acetate. The resulting copper salt was filtered, washed with hexane, and stirred with 6N hydrochloric acid to destroy the salt. The acidic aqueous solution was extracted with ether. The ether solution was then washed with water and dried over MgSO4. Concentration of the ether solution under vacuum afforded 4.4 g of the desired product as a brown oil (34.2% yield). The structure was confirmed by instrumental analysis.

Workup

  1. washThe solution was washed with 2 normal hydrochloric acid (2N HCl), 5% potassium carbonate solution, and saturated sodium chloride solution
  2. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  3. concentrationconcentrated under vacuum
  4. dissolutionThe residue was dissolved in 40 ml of acetonitrile
  5. stirringthe solution stirred for 1 hour at room temperature
  6. washAfter dilution with ether (150 ml), the solution was washed with 2N HCl
  7. stirringThe ether layer was then stirred with 100 ml of 5% copper (II) acetate
  8. filtrationThe resulting copper salt was filtered
  9. washwashed with hexane
  10. stirringstirred with 6N hydrochloric acid
  11. customto destroy the salt
  12. extractionThe acidic aqueous solution was extracted with ether
  13. washThe ether solution was then washed with water
  14. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-4cb149925bec4fffa3a8626570a0d0c7
Source dataset
uspto-grants-1989_01
Patent number
US04795488

Reaction notes

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