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

HRID 1362726Notes

Reaction equation

HRID 1362726 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-f596d3c6fb6d47e082d0bd58f4c51121
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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