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

HRID 1623046Notes

Reaction equation

HRID 1623046 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 (3.07 ml, 2.54 mol) of methylglyoxal dimethyl acetal (21) were stirred at 110° C. for 4 ours (h), together with 303 g (337 ml, 2.54 mol) of N,N-dimethylformamide dimethyl acetal (17). The methanol which was formed during the reaction was removed continuously from the reaction solution by distillation. After the reaction solution had cooled down, it was extracted with heptane and the solvent was evaporated. This resulted in 303 g of crude product 22 (yield 70%), which was reacted without any further purification.

Workup

  1. customwas removed continuously from the reaction solution by distillation
  2. temperatureAfter the reaction solution had cooled down
  3. extractionit was extracted with heptane
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-61ae3168daba4471836d74f929444277
Source dataset
uspto-grants-2014_07
Patent number
US08778955B2

Reaction notes

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