Water → HCID 5315074, compound

HRID 561473Notes

Reaction equation

HRID 561473 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[F:6][C:7]([F:17])([F:16])[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.O.C(OCC)(=O)C>C1COCC1.C(OCC)C>[CH:1]1([CH:12]([C:11]2[CH:10]=[CH:9][C:8]([C:7]([F:6])([F:16])[F:17])=[CH:15][CH:14]=2)[OH:13])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 679964-(Trifluoromethyl)benzaldehydeHCID 178418630HCID 178418630, compound

Product 1

HCID 5315074HCID 5315074, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

34 ml (17.2 mmol) of 0.5N cyclopropylmagnesium bromide solution in THF were added to 2.00 g (11.5 mmol) of 4-(trifluoromethyl)benzaldehyde in 44 ml of diethyl ether at 0° C., and the mixture was warmed to RT and stirred at RT overnight. The reaction mixture was added to water and ethyl acetate, the phases were separated, the aqueous phase was extracted twice with ethyl acetate, and the combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate 95/5) to result in 1.77 g (71% of theory) of the title compound.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted twice with ethyl acetate
  3. washthe combined organic phases were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate 95/5)

Sources & evidence

ORD record
ord-0610fff384ef42aab31c5920bdee3118
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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