Chloroform → 3-Hydroxy-2-[2-oxo-2-(3-trifluoromethylphenyl)ethyl]-5-phenylcyclohex-2-enone

HRID 229726Notes

Reaction equation

HRID 229726 reaction equation
C(Cl)(Cl)Cl.Br[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1)=[O:8].[C:19]1([CH:25]2[CH2:30][C:29](=[O:31])[CH2:28][C:27](=[O:32])[CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[OH:32][C:27]1[CH2:26][CH:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:30][C:29](=[O:31])[C:28]=1[CH2:6][C:7](=[O:8])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 5689621,3-Cyclohexanedione, 5-phenyl-HCID 27783862-Bromo-1-[3-(trifluoromethyl)phenyl]ethan-1-one

Product 1

HCID 230867203-Hydroxy-2-[2-oxo-2-(3-trifluoromethylphenyl)ethyl]-5-phenylcyclohex-2-enoneYield 35%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a chloroform solution (2 mL) of 2-bromo-3′-trifluoromethylacetophenone (534.1 mg, 2 mmol) and 5-phenyl-1,3-cyclohexanedione (376.5 mg, 2 mmol) was added potassium carbonate (276.4 mg, 2 mmol) and stirred under suspension at room temperature over night. The reaction liquid was added with ethyl acetate (5 mL), to filter off undissolved substance, followed by concentration of thus obtained organic layer under reduced pressure and purification of concentrated residue using silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain a crude product, which was further purified by suspension (hexane 1 ml/ethyl acetate about 0.2 ml) to obtain an objective compound (257.8 mg, 35.0%).

Workup

  1. customThe reaction liquid
  2. filtrationto filter off undissolved substance
  3. customfollowed by concentration of thus obtained organic layer under reduced pressure and purification of concentrated residue
  4. customto obtain a crude product, which
  5. customwas further purified by suspension (hexane 1 ml/ethyl acetate about 0.2 ml)

Sources & evidence

ORD record
ord-71568cb0282d4223baa1aa10a6db8389
Source dataset
uspto-grants-2009_07
Patent number
US07563893B2

Reaction notes

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