Water → Methyl 4-(3-fluorophenyl)-4-oxobutanoate

HRID 2103332Notes

Reaction equation

HRID 2103332 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[C:10]([O:14][CH3:15])(=[O:13])[CH:11]=[CH2:12].[C-]#N.[K+].O>CN(C)C=O>[CH3:15][O:14][C:10](=[O:13])[CH2:11][CH2:12][C:5]([C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[CH:3]=1)=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 7294Methyl AcrylateHCID 9032Potassium CyanideHCID 680093-Fluorobenzaldehyde

Product 1

HCID 12465650Methyl 4-(3-fluorophenyl)-4-oxobutanoateYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 3-fluorobenzaldehyde (35.38 g, 285.07 mml) in 35 mL dimethylformamide (DMF) was added to a heated (48° C.) solution of methyl acrylate (26.28 mL, 25.03 g, 290.7 mmol) and powdered KCN under Argon. The reaction mixture was stirred at 40° C. for 2 hours and then poured into 500 mL of water. This aqueous phase was extracted twice with 500 mL of Et2O and once with 250 mL of EtOAc. The combined organic layers were washed with water and saturated brine, and then dried over MgSO4. The solvent was evaporated under reduced pressure to give 50.89 g (242.2 mmol, 84.93%) of 4-(3-fluoro-phenyl)-4-oxo-butyric acid methyl ester as an oil. MS: 211 (M+H)+.

Workup

  1. extractionThis aqueous phase was extracted twice with 500 mL of Et2O and once with 250 mL of EtOAc
  2. washThe combined organic layers were washed with water and saturated brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0e70545cb9cb4a1c8f0d591fc9e27d0b
Source dataset
uspto-grants-2009_08
Patent number
US07576103B2

Reaction notes

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