1,1,1-Trifluoro-4-methylpent-3-en-2-one → HCID 46938919, compound

HRID 2106012Notes

Reaction equation

HRID 2106012 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Mg]Br.[CH3:11][C:12]([CH3:20])=[CH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16]>C(OCC)C.[Cu]I>[F:16][C:15]([F:18])([F:17])[C:14](=[O:19])[CH2:13][C:12]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])([CH3:20])[CH3:11]

Participants

5

Reactant 2

HCID 220326911,1,1-Trifluoro-4-methylpent-3-en-2-oneHCID 178489560HCID 178489560, compound

Product 1

HCID 46938919HCID 46938919, compoundYield 82%

Reagents, catalysts & solvents 2

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

Procedure

To a solution of 2-methoxyphenylmagnesium bromide (131 mL, 65.7 mmol, 0.5M solution in THF) at 0° C. was added CuI (12.5 g, 65.7 mmol). The reaction mixture was warmed to room temperature and stirred for 1 hour. A solution of 4-methyl-1,1,1-trifluoropent-3-en-2-one (10.0 g, 65.74 mmol) (made via procedure in PCT international application WO03/082280, Example 10), in diethyl ether (200 mL) was added and the reaction mixture was stirred overnight. The reaction was quenched with saturated aqueous ammonium chloride (50 mL) and extracted with three 300 mL portions of ethyl acetate. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography using 0%-5% ethyl acetate in hexanes as the eluent. Concentration in vacuo of the product-rich fractions gave 14 g (82%) of 1,1,1-trifluoro-4-(2-methoxyphenyl)-4-methylpentan-2-one.

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. customThe reaction was quenched with saturated aqueous ammonium chloride (50 mL)
  3. extractionextracted with three 300 mL portions of ethyl acetate
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography
  9. concentrationConcentration in vacuo of the product-rich fractions

Sources & evidence

ORD record
ord-45c828f16c204209860bb6dc53a916f4
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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