Water → HCID 58392304, compound

HRID 561471Notes

Reaction equation

HRID 561471 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[Cl:6][C:7]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10].O.C(OCC)(=O)C>C1COCC1.C(OCC)C>[CH:1]1([CH:9]([C:8]2[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:7]=2[Cl:6])[OH:10])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 134042,4-DichlorobenzaldehydeHCID 178418630HCID 178418630, compound

Product 1

HCID 58392304HCID 58392304, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

17 ml (8.57 mmol) of 0.5N cyclopropylmagnesium bromide solution in THF were added to 1.00 g (5.71 mmol) of 2,4-dichlorobenzaldehyde in 20 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 preparative HPLC (RP18 column; mobile phase: acetonitrile/water) to result in 925 mg (74% 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 preparative HPLC (RP18 column; mobile phase: acetonitrile/water)

Sources & evidence

ORD record
ord-8d43fd27526544f7a773c4252225df27
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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