Dimethylformamide dimethyl acetal → 1-Penten-3-one, 1-(dimethylamino)-4,4-dimethoxy-

HRID 1623045Notes

Reaction equation

HRID 1623045 reaction equation
[CH3:1][O:2][C:3]([O:8][CH3:9])([CH3:7])[C:4](=[O:6])[CH3:5].CO[CH:12](OC)[N:13]([CH3:15])[CH3:14]>CO>[CH3:12][N:13]([CH3:15])[CH:14]=[CH:5][C:4](=[O:6])[C:3]([O:8][CH3:9])([O:2][CH3:1])[CH3:7]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 1408713,3-Dimethoxy-2-butanone

Product 1

HCID 5668111-Penten-3-one, 1-(dimethylamino)-4,4-dimethoxy-Yield 90.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

100 g (0.76 mol) of 3,3-dimethoxy-2-butanone (16) were stirred together with 90.2 g of N,N-dimethylformamide dimethyl acetal (17) (0.76 mol) at 120° C. for 48 h. The methanol which was formed in the reaction was removed continuously from the reaction solution by means of distillation. Crystallization occurred spontaneously when the solution was cooled, with the crystallization being brought to completion by adding a little heptane. This resulted in 128.24 g of crude product 18 (yield 90%), which was reacted without any further purification.

Workup

  1. customwas removed continuously from the reaction solution by means of distillation
  2. customCrystallization
  3. temperaturewas cooled, with the crystallization
  4. additionby adding a little heptane

Sources & evidence

ORD record
ord-825c72230d9c43feac0c79a4a2c44c21
Source dataset
uspto-grants-2014_07
Patent number
US08778955B2

Reaction notes

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