Dimethylformamide dimethyl acetal → ((1E)-4,4-dimethoxy-3-oxobut-1-en-1-yl)dimethylamine

HRID 1397001Notes

Reaction equation

HRID 1397001 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[CH3:9][O:10][CH:11]([O:15][CH3:16])[C:12](=[O:14])[CH3:13]>>[CH3:3][N:4]([CH3:6])/[CH:5]=[CH:13]/[C:12](=[O:14])[CH:11]([O:15][CH3:16])[O:10][CH3:9]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 80650Pyruvic aldehyde dimethyl acetal

Product 1

HCID 5709580((1E)-4,4-dimethoxy-3-oxobut-1-en-1-yl)dimethylamineYield 91.4%

Conditions

Temperature
110 °C

Procedure

1,1-dimethoxy-N,N-dimethylmethanamine (100 g, 839 mmol, 1.02 equiv.) and 1,1-dimethoxypropan-2-one (97 g, 821 mmol) were added and stirred at 110° C. for 3 hours. The produced methanol was removed by a Dean-Stark apparatus. After the solution was cooled to room temperature, the remaining volatile materials were removed in vacuo to provide 130 g of the crude product, (E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one (1) (130 g, 143 g theoretical, 91%). LC-MS m/z 283 (M+1). Reference: WO 2006/0097341A1 (incorporated by reference), pg 67.

Workup

  1. customThe produced methanol was removed by a Dean-Stark apparatus
  2. temperatureAfter the solution was cooled to room temperature
  3. customthe remaining volatile materials were removed in vacuo

Sources & evidence

ORD record
ord-06e3fa3c87404741a2ff00af864035d5
Source dataset
uspto-grants-2014_12
Patent number
US08901145B2

Reaction notes

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