Toluene → HCID 89767734, compound

HRID 591525Notes

Reaction equation

HRID 591525 reaction equation
[C:1]([CH:4]([CH2:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=O)[CH3:2].C1(C)C=CC=CC=1>O>[CH3:2][C:1]1[O:16][C:11]([C:12]([F:13])([F:14])[F:15])=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 1140TolueneHCID 89767759HCID 89767759, compound

Product 1

HCID 89767734HCID 89767734, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of ethyl 2-acetyl-5,5,5-trifluoro-4-oxopentanoate (1.37 g) and toluene (5 mL) was added TsOH monohydrate (0.109 g) at room temperature, and the mixture was refluxed with azeotropic removal of water by Dean-Stark apparatus for 14 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (0.730 g).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-85f952df74b64a4c9795b9944d7f3851
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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