Dimethylformamide → (E)-3-Dimethylamino-1-phenyl-propenone

HRID 514360Notes

Reaction equation

HRID 514360 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:10][N:11]([CH:13]=O)[CH3:12]>CC(N(C)C)=O>[CH3:10][N:11]([CH3:13])/[CH:12]=[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 6228DimethylformamideHCID 7410Acetophenone

Product 1

HCID 5398495(E)-3-Dimethylamino-1-phenyl-propenoneYield 29.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of acetophenone (8.0 g, 66.58 mmol, 1.0 eq) and DMF (5.8 g, 79.90 mmol, 1.2 eq.) in 10.0 mL of DMA in a 25-mL microwave vial was irradiated at 115° C. for 0.5-1 h. The crude reaction mixture was triturated with n-hexane, and the resultant solid was filtered to afford the title compound as a pale yellow solid (3.4 g. 29.3% yield). [M+H] Calc'd for C11H13NO, 176. Found, 176.

Workup

  1. customwas irradiated at 115° C. for 0.5-1 h
  2. customThe crude reaction mixture
  3. customwas triturated with n-hexane
  4. filtrationthe resultant solid was filtered

Sources & evidence

ORD record
ord-939f106951474b73be6ddcbd06113665
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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