Tetrahydrofuran → Hexafluoroacetylacetone

HRID 1980076Notes

Reaction equation

HRID 1980076 reaction equation
[C:1]([C:5]([CH2:7]Br)=[O:6])([F:4])([F:3])[F:2].[C:9]([C:13](OCC)=[O:14])([F:12])([F:11])[F:10].O1CCCC1>[Zn].CN(C)C=O>[C:1]([C:5]([CH2:7][C:13]([C:9]([F:12])([F:11])[F:10])=[O:14])=[O:6])([F:4])([F:3])[F:2]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 9794Ethyl trifluoroacetateHCID 790083-Bromo-1,1,1-trifluoro-2-propanone

Product 1

HCID 73706Hexafluoroacetylacetone

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Procedure

CF3COCH2Br (1.91 gr, 10 mmol), CF3CO2C2H5 (1.42 gr, 10 mmol), and zinc powder (1.3 gr) were put into a flask (100 ml) together with a mixed solvent comprising tetrahydrofuran (20 ml) and dimethylformamide (10 ml), and they were subjected to the reaction for a period of one hour while being irradiated with ultrasonic waves by means of an ultrasonic cleaner (35W, 32 kHz). After the reaction, impurities contained in the mixed liquid were filtered, then water (500 ml) was added to the filtered liquid, whereby an oil layer generated was extracted by means of diethylether. After drying the extracted liquid with magnesium sulfate, the solvent was removed. The product (CF3COCH2COCF3) (bp: 70° to 72° C.) was obtained through distillation with a yield by 69%.

Workup

  1. customAfter the reaction, impurities
  2. filtrationwere filtered
  3. additionwater (500 ml) was added to the filtered liquid, whereby an oil layer
  4. extractiongenerated was extracted by means of diethylether
  5. dry with materialAfter drying the extracted liquid with magnesium sulfate
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-6f1e31e9d1374a04b229186fdc8fcf24
Source dataset
uspto-grants-1984_11
Patent number
US04484993

Reaction notes

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