Water → 1-(3-Fluorophenyl)-4-methyl-2-pentanol

HRID 2390056Notes

Reaction equation

HRID 2390056 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH2:11]([Mg]Br)[CH:12]([CH3:14])[CH3:13].O>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([OH:10])[CH2:11][CH:12]([CH3:14])[CH3:13])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 15811999(3-Fluorophenyl)acetaldehydeHCID 178418816HCID 178418816, compound

Product 1

HCID 593233911-(3-Fluorophenyl)-4-methyl-2-pentanolYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

97 mg of 3-fluorobenzeneacetaldehyde and 0.386 mL of isobutyl magnesium bromide (2 M/diethyl ether solution) were dissolved in of 0.2 mL of THF, followed by stirring at room temperature for 1 hour. After completion of the reaction, water was added to the reaction liquid, followed by extraction with chloroform, and the organic layer was then washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified using PLC (ethyl acetate:hexane=1:2) to obtain 102 mg (yield 74%) of a title compound as a pale yellow oily substance.

Workup

  1. additionwas added to the reaction liquid
  2. extractionfollowed by extraction with chloroform
  3. washthe organic layer was then washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified

Sources & evidence

ORD record
ord-b7939bf8bc9246089c7d15942dfe8c5e
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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