1-(p-Methoxyphenyl)-2-propanone → 4-Dimethylamino-3-(4-methoxyphenyl)-3-buten-2-one

HRID 11320

Reaction equation

HRID 11320 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:12])[CH3:11])=[CH:5][CH:4]=1.OC[CH2:15][N:16]1[C:20](=O)C2=CC=CC=C2[C:17]1=O>CN(C)C=O>[CH3:15][N:16]([CH3:20])[CH:17]=[C:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:10](=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 312311-(p-Methoxyphenyl)-2-propanoneHCID 77499N-(2-Hydroxyethyl)phthalimide

Product 1

HCID 539901024-Dimethylamino-3-(4-methoxyphenyl)-3-buten-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 1-(4-methoxy-phenyl)-propan-2-one (1, 8.37 g, 51.0 mmol) in N,N-dimethylformamide (200 mL) was added dimethoxymethyl-dimethyl-amine (2, 27 mL, 203 mmol). The reaction mixture was then stirred for 18 h at 85° C., allowed to cool to ambient temperature and excess solvent and reagents were removed under reduced pressure to give crude 4-dimethylamino-3-(4-methoxyphenyl)-but-3-en-2-one (3) as yellow oil which was used in the following step without further purification.

Workup

  1. temperatureto cool to ambient temperature
  2. customexcess solvent and reagents were removed under reduced pressure

Sources & evidence

ORD record
ord-ba9cd433d44c4544b97682e7fc2afe04
Source dataset
uspto-grants-2006_08
Patent number
US07098211B2

Linked notes

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