Ether tetrahydrofuran → 1,1,1-Trifluoro-4-(4-fluorophenyl)-4-methylpentan-2-one

HRID 1791336Notes

Reaction equation

HRID 1791336 reaction equation
CCOCC.C1COCC1.[F:11][C:12]([F:20])([F:19])[C:13](=[O:18])[CH:14]=[C:15]([CH3:17])[CH3:16].[F:21][C:22]1[CH:27]=[CH:26][C:25]([Mg]Br)=[CH:24][CH:23]=1>[Cu]I.CCOCC>[F:11][C:12]([F:20])([F:19])[C:13](=[O:18])[CH2:14][C:15]([C:25]1[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=1)([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 21868444Ether tetrahydrofuranHCID 220326911,1,1-Trifluoro-4-methylpent-3-en-2-oneHCID 178418676HCID 178418676, compound

Product 1

HCID 220326931,1,1-Trifluoro-4-(4-fluorophenyl)-4-methylpentan-2-one

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent

Procedure

To a 2 M ether/THF solution of the above 1,1,1-trifluoro-4-methylpent-3-en-2-one was added 3.8 g of CuI and 10 mL of 2 M ether solution of 4-fluorophenylmagnesium bromide at 0° C. The mixture was warmed to room temperature and stirred for 2 hours. The reaction was quenched with saturated aqueous ammonium chloride and extracted with EtOAc three times. The combined organic layers were washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography to yield 460 mg of the title compound.

Workup

  1. customThe reaction was quenched with saturated aqueous ammonium chloride
  2. extractionextracted with EtOAc three times
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-1f92c4dbb5644799998fc794518485ad
Source dataset
uspto-grants-2006_07
Patent number
US07074806B2

Reaction notes

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