(3S)-3-phenylbutanoic acid → (S)-4-Phenylpentan-2-one

HRID 1366932

Reaction equation

HRID 1366932 reaction equation
[CH3:1][Li].[C:3]1([C@@H:9]([CH3:14])[CH2:10][C:11]([OH:13])=O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CCOCC>[C:3]1([C@@H:9]([CH3:14])[CH2:10][C:11](=[O:13])[CH3:1])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 852991(3S)-3-phenylbutanoic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 11008238(S)-4-Phenylpentan-2-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.6 M Methyl lithium (17.8 mL, 24.9 mmol) was added over 1 hour to a stirring 0° C. solution of (S)-3-Phenylbutyric acid (2.0147 g, 12.18 mmol) in dry Et2O (61 mL, 0.2 M): The ice bath was removed, and the reaction was allowed to stir at room temperature for 1½ additional hours. The reaction was then poured into rapidly stirring ice water containing aq. HCl. The organic layer was removed, washed with NaHCO3 and brine, then dried with Na2SO4, filtered and concentrated to achieve pure 77 (2.0487 g, (2.0487 g, ˜100%): HPLC: 10.081 min. (Note: SM has HPLC retention time of 9.127 min.)

Workup

  1. customThe ice bath was removed
  2. additionThe reaction was then poured into rapidly stirring ice water containing aq. HCl
  3. customThe organic layer was removed
  4. washwashed with NaHCO3 and brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custom10.081 min. (Note: SM has HPLC retention time of 9.127 min.)

Sources & evidence

ORD record
ord-01034d53eb2648ed9b07c6cf0e9f068f
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Linked notes

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