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

HRID 1348527Notes

Reaction equation

HRID 1348527 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, 1 H, J=3.9 & 4.9); 7.77 (dd, 1 H, J=1.1 & 4.9 Hz); 7.85 (dd, 1 H, 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-92a6ac4c660741eba4d2140a5c81a379
Source dataset
uspto-grants-2007_05
Patent number
US07211440B2

Reaction notes

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