Hydrochloric Acid → 1-Methyl-4-(5,5,5-trifluoro-3-methylpent-1-en-2-yl)benzene

HRID 877198Notes

Reaction equation

HRID 877198 reaction equation
[CH3:1][Mg]I.[F:4][C:5]([F:19])([F:18])[CH2:6][CH:7]([CH3:17])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)=O.Cl>C(OCC)C>[CH3:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]([CH:7]([CH3:17])[CH2:6][C:5]([F:19])([F:18])[F:4])=[CH2:1])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 581365984,4,4-Trifluoro-2-methyl-1-(4-methylphenyl)butan-1-oneHCID 178418373HCID 178418373, compound

Product 1

HCID 581364211-Methyl-4-(5,5,5-trifluoro-3-methylpent-1-en-2-yl)benzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent4×

Procedure

Under argon, 1.45 ml (4.34 mmol) of a 3 M solution of methylmagnesium iodide in diethyl ether were initially charged in 10 ml of diethyl ether, and 1000 mg (4.34 mmol) of 4,4,4-trifluoro-2-methyl-1-(4-methylphenyl)butan-1-one, dissolved in 5 ml of diethyl ether, were added slowly at 0 C. The reaction mixture was then slowly warmed to room temperature and stirred overnight. The reaction solution was then slowly added to 15 ml of 1 M hydrochloric acid and diluted with diethyl ether. After removal of the organic phase, the aqueous phase was extracted three more times with diethyl ether. The combined organic phases were dried over magnesium sulfate and filtered, and the solvent was removed under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 50:1). This gave 710 mg (3.11 mmol, 71% of theory) of the title compound as a colorless oil.

Workup

  1. additionwere added slowly at 0 C
  2. customAfter removal of the organic phase
  3. extractionthe aqueous phase was extracted three more times with diethyl ether
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 50:1)

Sources & evidence

ORD record
ord-4947bda62108431eb22df2149e2fbd11
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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