Ethyl Acetate → 1-(4-Fluoro-3-methoxyphenyl)ethan-1-ol

HRID 1446582Notes

Reaction equation

HRID 1446582 reaction equation
C[Mg]Cl.[F:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[O:13][CH3:14].[Cl-].[NH4+].[C:17](OCC)(=O)C>C1COCC1>[F:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]([OH:10])[CH3:17])=[CH:7][C:6]=1[O:13][CH3:14]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 27373584-Fluoro-3-methoxybenzaldehydeHCID 178418332HCID 178418332, compound

Product 1

HCID 247215201-(4-Fluoro-3-methoxyphenyl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl magnesium chloride (3 M tetrahydrofuran solution, 7.8 mL) was added to a solution of 4-fluoro-3-methoxybenzaldehyde (3 g) in THF (200 mL) while cooling with ice, and the reaction solution was stirred for 2 hours while cooling with ice. A saturated aqueous solution of ammonium chloride and ethyl acetate were added to the reaction solution and the organic layer was partitioned. The resulting organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (Carrier: Chromatorex™ NH, elution solvent:heptane-ethyl acetate system) to obtain 2.65 g of the title compound. The physical properties of the compound are as follows.

Workup

  1. temperaturewhile cooling with ice
  2. temperaturewhile cooling with ice
  3. customthe organic layer was partitioned
  4. dry with materialThe resulting organic layer was dried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (Carrier: Chromatorex™ NH, elution solvent:heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-a8f4b0c274454b47a0566162da83cc2c
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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