Dimethylformamide dimethyl acetal → (2E)-1-[2-(allyloxy)-4-methylphenyl]-3-(dimethylamino)prop-2-en-1-one

HRID 2406394Notes

Reaction equation

HRID 2406394 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[C:12](=[O:14])[CH3:13])[CH:2]=[CH2:3].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>>[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[C:12](=[O:14])/[CH:13]=[CH:17]/[N:18]([CH3:20])[CH3:19])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 607470631-[2-(Allyloxy)-4-methylphenyl]ethanone

Product 1

HCID 69672943(2E)-1-[2-(allyloxy)-4-methylphenyl]-3-(dimethylamino)prop-2-en-1-one

Procedure

To 1-[2-(allyloxy)-4-methylphenyl]ethanone (Step 1, 13.9 g, 73 mmol) was added dimethylformamide dimethylacetal (56 mL, 422 mmol), and the reaction was heated to reflux for 18 hours. The reaction was then concentrated in vacuo to give the title compound as an orange oil, 17.9 g, which was taken crude into the next reaction.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 18 hours
  3. concentrationThe reaction was then concentrated in vacuo

Sources & evidence

ORD record
ord-10e40a3dbff94912a2b257f51ece45da
Source dataset
uspto-grants-2014_08
Patent number
US08809363B2

Reaction notes

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