Sulfuric Acid → HCID 178520888, compound

HRID 890477Notes

Reaction equation

HRID 890477 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]([F:20])([F:19])[O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=1.[F:21][C:22]([F:29])([F:28])[C:23](OCC)=[O:24].OS(O)(=O)=O>C1(C)C=CC=CC=1>[F:21][C:22]([F:29])([F:28])/[C:23](/[OH:24])=[CH:17]/[C:16]([C:13]1[CH:12]=[CH:11][C:10]([O:9][C:8]([F:19])([F:20])[F:7])=[CH:15][CH:14]=1)=[O:18]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 9794Ethyl trifluoroacetateHCID 5228211-(4-(Trifluoromethoxy)phenyl)ethan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 178520888HCID 178520888, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a toluene (50 ml) suspension of potassium t-butoxide (3.3 g, 29 mmol) and 1-(4-trifluoromethoxy-phenyl)-ethanone (3.9 ml, 24 mmol) under an argon atmosphere was added dropwise ethyl trifluoroacetate (3.4 ml, 29 mmol) at 10° C. The suspension was stirred at ambient temperature for 14 h. The pH value of the mixture was adjusted to 6 with 10% H2SO4, the solution was extracted two times with t-butyl methylether and the combined extracts were washed with brine/ice water 1/1. The organic layer was dried over sodium sulfate, concentrated under reduced pressure and the residue purified by column chromatography (silica gel, n-heptane/ethyl acetate) to yield 2.9 g (9.7 mmol, 40%) of the title compound as orange oil.

Workup

  1. extractionthe solution was extracted two times with t-butyl methylether
  2. washthe combined extracts were washed with brine/ice water 1/1
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe residue purified by column chromatography (silica gel, n-heptane/ethyl acetate)

Sources & evidence

ORD record
ord-e5add8599384426bbe35982286760510
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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