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

HRID 457274Notes

Reaction equation

HRID 457274 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 and 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 and 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-0e5ebbdb3cd14989975be7de15ce631a
Source dataset
uspto-grants-2007_03
Patent number
US07186864B2

Reaction notes

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