Methanol → 4-(Dimethylamino)-1,1-dimethoxybut-3-en-2-one

HRID 2406284Notes

Reaction equation

HRID 2406284 reaction equation
[CH3:1][O:2][C:3]([O:7][CH3:8])(C)[CH:4]=[O:5].CO[CH:11](OC)[N:12]([CH3:14])[CH3:13].[CH3:17]O>>[CH3:13][N:12]([CH3:14])[CH:11]=[CH:17][C:4](=[O:5])[CH:3]([O:7][CH3:8])[O:2][CH3:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 78373Dimethylformamide dimethyl acetalHCID 75681812,2-Dimethoxypropanal

Product 1

HCID 27821454-(Dimethylamino)-1,1-dimethoxybut-3-en-2-oneYield 70%

Procedure

300 g (307 ml, 2.54 mol) of methylglyoxal dimethylacetal were stirred, at 110° C. for 4 hours (h), with 303 g (337 ml, 2.54 mol) of N,N-dimethylformamide dimethylacetal. The methanol which was formed during the reaction was removed continuously from the reaction solution by distillation. After having been cooled down, the solution was extracted with heptane and the solvents were evaporated. This resulted in 303 g of crude product 16 (yield 70%), which was reacted without any further purification.

Workup

  1. customwas removed continuously from the reaction solution by distillation
  2. temperatureAfter having been cooled down
  3. extractionthe solution was extracted with heptane
  4. customthe solvents were evaporated

Sources & evidence

ORD record
ord-f2901702cefd41ed9a6d296a6311a0c2
Source dataset
uspto-grants-2014_08
Patent number
US08809358B2

Reaction notes

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