Dimethylformamide dimethyl acetal → Methyl 4-[3-(dimethylamino)prop-2-enoyl]benzoate

HRID 1873993Notes

Reaction equation

HRID 1873993 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>CO>[CH3:16][N:17]([CH3:19])/[CH:18]=[CH:2]/[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 137990Methyl 4-acetylbenzoate

Product 1

HCID 10561611Methyl 4-[3-(dimethylamino)prop-2-enoyl]benzoateYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of methyl 4-acetylbenzoate (25 g, 140 mmol) and N,N-dimethylformamide dimethyl acetal (100 mL) was heated to reflux for 2 days, diluted with MeOH (100 mL) and cooled to 0° C. The precipitate was collected by filtration and washed with MeOH to give (E)-methyl 4-(3-(dimethylamino)acryloyl)benzoate as a brown solid (27.65 g, 84% yield). MS (ES+) m/z: 234 (M+H); LC retention time: 2.91 min (analytical HPLC Method A).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 days
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with MeOH

Sources & evidence

ORD record
ord-941d754394294eca92910effdefa6fa0
Source dataset
uspto-grants-2012_11
Patent number
US08304539B2

Reaction notes

Loading…