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

HRID 2188197Notes

Reaction equation

HRID 2188197 reaction equation
[C-]#N.[K+].[F:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9].[C:13]([O:17][CH2:18]C)(=[O:16])[CH:14]=[CH2:15].O>CN(C)C=O>[CH3:18][O:17][C:13](=[O:16])[CH2:14][CH2:15][C:8]([C:7]1[CH:10]=[CH:11][CH:12]=[C:5]([F:4])[CH:6]=1)=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8821Ethyl AcrylateHCID 9032Potassium CyanideHCID 680093-Fluorobenzaldehyde

Product 1

HCID 12465650Methyl 4-(3-fluorophenyl)-4-oxobutanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To a stirred suspension of potassium cyanide (3.25 g) in N,N-dimethylformamide (30 cm3), being maintained at a temperature of 45° C., was added 3-fluorobenzaldehyde (25.0 g). Ethyl acrylate (18.46 cm3) was then added and the resultant mixture was stirred at 40° C. for 2 h. Water (200 cm3) was added and the aqueous mixture was extracted with diethyl ether (2×125 cm3). The organic extracts were washed with water (100 cm3) and saturated aqueous sodium chloride solution (100 cm3) before being dried (Na2SO4) and the solvent was removed under reduced pressure to yield the title compound (25.27 g) as a yellow oil.

Workup

  1. extractionthe aqueous mixture was extracted with diethyl ether (2×125 cm3)
  2. washThe organic extracts were washed with water (100 cm3) and saturated aqueous sodium chloride solution (100 cm3)
  3. dry with materialbefore being dried (Na2SO4)
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0d97eeb0a4084603b84111e3f241efc4
Source dataset
uspto-grants-2002_06
Patent number
US06410592B1

Reaction notes

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