Dimethylformamide dimethyl acetal → 4-(Dimethylamino)-1,1-dimethoxybut-3-en-2-one

HRID 2202117Notes

Reaction equation

HRID 2202117 reaction equation
[CH3:1][O:2][CH:3]([O:7][CH3:8])[C:4](=[O:6])[CH3:5].[CH3:9][N:10]([CH:12](OC)OC)[CH3:11]>>[CH3:9][N:10]([CH3:12])[CH:11]=[CH:5][C:4](=[O:6])[CH:3]([O:7][CH3:8])[O:2][CH3:1]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 80650Pyruvic aldehyde dimethyl acetal

Product 1

HCID 27821454-(Dimethylamino)-1,1-dimethoxybut-3-en-2-oneYield 123.7%

Conditions

Temperature
100 °C

Procedure

A mixture of 1,1-dimethoxypropan-2-one (10 g, 84.65 mmol, 1.00 equiv) and DMF-DMA (10 g, 84.03 mmol, 0.99 equiv) was stirred at 100° C. for 5 h. The resulting mixture was cooled to room temperature and concentrated under vacuum to give 18 g of crude 4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one as a brown liquid. The crude product was used in the next step without further purification.

Workup

  1. temperatureThe resulting mixture was cooled to room temperature
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-852f3a3b03b24823833953693f6efea0
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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