Sulfuric Acid → 4,4,5,5,5-Pentafluoro-1-(thiophen-2-yl)pentane-1,3-dione

HRID 130293Notes

Reaction equation

HRID 130293 reaction equation
[C:1]([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)(=[O:3])[CH3:2].[H-].[Na+].[F:11][C:12]([F:22])([F:21])[C:13]([F:20])([F:19])[C:14](OCC)=[O:15].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[F:19][C:13]([F:20])([C:12]([F:22])([F:21])[F:11])[C:14](=[O:15])[CH2:2][C:1]([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)=[O:3]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 69202-AcetylthiopheneHCID 24758Sodium hydrideHCID 67928Propanoic acid, 2,2,3,3,3-pentafluoro-, ethyl ester

Product 1

HCID 170246234,4,5,5,5-Pentafluoro-1-(thiophen-2-yl)pentane-1,3-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Acetylthiophene (4.3 ml) was dissolved in dry toluene (40 ml). Sodium hydride (60%, 3.2 g) was added slowly and the mixture was stirred for 15 minutes. Ethyl pentafluoropropionate (13.44 g) was added and the stirring was continued overnight. Sulfuric acid (10%, 50 ml) was added and the phases were separated. The organic phase was washed with water (50 ml) and it was evaporated to dryness. The residue was distilled (b.p. 92-94° C./0.15 mbar) to give the product (9.0 g). 1H NMR (CDCl3): 6.50 (s, 1 H); 7.21 (dd, 1H, J=3.9 & 4.9); 7.77 (dd, 1H, J=1.1 & 4.9 Hz); 7.85 (dd, 1H, J=1.1 & 3.9 Hz). IR (film): 1592 (C═O); 1202 (C—F).

Workup

  1. waitthe stirring was continued overnight
  2. customthe phases were separated
  3. washThe organic phase was washed with water (50 ml) and it
  4. customwas evaporated to dryness
  5. distillationThe residue was distilled (b.p. 92-94° C./0.15 mbar)

Sources & evidence

ORD record
ord-4035447da51f4952a025db1eac0e4fb5
Source dataset
uspto-grants-2008_06
Patent number
US07381567B2

Reaction notes

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