1-(4-(Trifluoromethyl)phenyl)ethan-1-one → HCID 15428868, compound

HRID 1108565Notes

Reaction equation

HRID 1108565 reaction equation
CC(C)([O-])C.[K+].[CH:7]1([C:12]([O:14]C)=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:26])[CH3:25])=[CH:20][CH:19]=1>O1CCCC1.C1OCCOCCOCCOCCOCCOC1>[CH:7]1([C:12](=[O:14])[CH2:25][C:24]([C:21]2[CH:22]=[CH:23][C:18]([C:17]([F:16])([F:27])[F:28])=[CH:19][CH:20]=2)=[O:26])[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

6

Reactant 3

HCID 697311-(4-(Trifluoromethyl)phenyl)ethan-1-oneHCID 78365Methyl cyclopentanecarboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 15428868HCID 15428868, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.97 kg of potassium tert-butoxide, 2.26 kg of methyl cyclopentanecarboxylate, 1.66 kg of p-trifluoromethylacetophenone and 36 g of 18-crown-6 ether were refluxed in 18 litres of tetrahydrofuran for 4 hours. Quenching of the reaction was carried out using 16 litres of 10% strength hydrochloric acid at room temperature. The aqueous phase was extracted with ethyl acetate and the combined organic phases were washed with saturated sodium chloride solution. After distilling off the solvent, the residue was distilled in an oil-pump vacuum at 1.5 mbar. 1.664 kg of 1-cyclopentyl-3-(4-trifluoromethylphenyl)propane-1,3-dione resulted as an oil, which crystallized completely on allowing to stand.

Workup

  1. customQuenching of the reaction
  2. customat room temperature
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organic phases were washed with saturated sodium chloride solution
  5. distillationAfter distilling off the solvent
  6. distillationthe residue was distilled in an oil-pump vacuum at 1.5 mbar

Sources & evidence

ORD record
ord-d03a78e7bc764776a198da1c3df55d15
Source dataset
uspto-grants-2000_05
Patent number
US06069148

Reaction notes

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