Acetophenone → 3-(Dimethylamino)-1-phenyl-2-propen-1-one

HRID 1355684Notes

Reaction equation

HRID 1355684 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CO[CH:12](OC)[N:13]([CH3:15])[CH3:14]>CN(C=O)C>[CH3:12][N:13]([CH3:15])[CH:14]=[CH:2][C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 7410AcetophenoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 3534603-(Dimethylamino)-1-phenyl-2-propen-1-oneYield 85.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5.0 ml (42.8 mmol) acetophenone in 40 ml DMF was added 11.4 ml (85.6 mmol) N,N-dimethylformamide dimethyl acetal and the mixture heated at reflux for 16 h. The reaction mixture was then concentrated in vacuo. Trituration in hexane/ethyl acetate (4/1) afforded 6.4 g (85%) 3-(dimethylamino)acrylophenone as a crystalline solid. EI-MS m/e (%): 175 (M+, 45), 158 ([M—OH]+, 100), 98 ([M—C6H5)+, 63), 42 (72).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 16 h
  3. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-9a246abe17124cb7b6abc9f1e254787e
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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