Potassium Carbonate → HCID 86757819, compound

HRID 1700924Notes

Reaction equation

HRID 1700924 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3](=[O:13])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>CC(C)=O.C1(C)C=CC=CC=1>[F:1][C:2]([F:14])([F:15])[C:3](=[O:13])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 18319102HCID 18319102, compound

Product 1

HCID 86757819HCID 86757819, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Conditions

Temperature
22 °C

Procedure

A solution of (E)-1,1,1-trifluoro-4-(4-hydroxyphenyl) 3-buten-2-one (0.105 g, 0.49 mmol) in acetone (6 ml) was treated with powdered potassium carbonate (0.3 g) and tert-butyl bromoacetate (0.20 g, 1.02 mmol) and stirred at 22° C. for 3 h. The reaction mixture was then diluted with toluene, washed with brine, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was chromatographed on silica gel (elution toluene-ethyl acetate 2%) and gave 0.150 g (94%) of the title material as yellow needles: mp 112-113° C.

Workup

  1. washwashed with brine
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was chromatographed on silica gel (elution toluene-ethyl acetate 2%)

Sources & evidence

ORD record
ord-ad7bd1ee6cc34c9db8dfcd0d7ca6a144
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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