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

HRID 1988150Notes

Reaction equation

HRID 1988150 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 1,1,1-trifluoro-4-methylpent-3-en-2-one was added 3.8 g of copper (I) iodide and 10 mL of a 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 NH4Cl, and extracted three times with EtOAc. 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 1,1,1-trifluoro-4-(4-fluorophenyl)-4-methylpentan-2-one.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted three times with EtOAc
  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-2d368501367a4e7ba4af520c9889577e
Source dataset
uspto-grants-2009_06
Patent number
US07553966B2

Reaction notes

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