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

HRID 2374472Notes

Reaction equation

HRID 2374472 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-a9ecadfb409940b48f21b78d62ad6684
Source dataset
uspto-grants-2008_12
Patent number
US07462638B2

Reaction notes

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