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

HRID 2406282Notes

Reaction equation

HRID 2406282 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 were stirred, at 120° C. for 48 h, with 90.2 g of N,N-dimethylformamide dimethylacetal (0.76 mol). The methanol which was formed during the reaction was continuously removed from the reaction solution by distillation. When the solution was cooled, spontaneous crystallization occurred, with this crystallization being brought to completion by adding a little heptane. This resulted in 128.24 g of crude product 8 (yield 90%), which was subjected to reaction without any further purification.

Workup

  1. customwas continuously removed from the reaction solution by distillation
  2. temperatureWhen the solution was cooled
  3. customspontaneous crystallization
  4. customoccurred, with this crystallization
  5. additionby adding a little heptane

Sources & evidence

ORD record
ord-630d1ca56941431cbd5e639b6d742156
Source dataset
uspto-grants-2014_08
Patent number
US08809358B2

Reaction notes

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