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

HRID 2105125Notes

Reaction equation

HRID 2105125 reaction equation
[CH3:1][O:2][CH:3]([O:7][CH3:8])[C:4](=[O:6])[CH3:5].CO[CH:11](OC)[N:12]([CH3:14])[CH3:13]>>[CH3:1][O:2][CH:3]([O:7][CH3:8])[C:4](=[O:6])[CH:5]=[CH:11][N:12]([CH3:14])[CH3:13]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 80650Pyruvic aldehyde dimethyl acetal

Product 1

HCID 27821454-(Dimethylamino)-1,1-dimethoxybut-3-en-2-oneYield 99.4%

Conditions

Temperature
100 °C

Procedure

1,1-Dimethoxypropan-2-one (57.9 g, 0.459 mol) was added to dimethyl formamide dimethyl acetal (54.6 g, 0.459 mol) and the mixture stirred and heated at 100° C. for 18 hours. The reaction mixture was allowed to cool and the volatiles removed by evaporation give the itle compound (79 g) as a red oil. NMR: (CDCl3): 2.90 (d, 3H), 3.10 (d, 3H), 3.40 (s, 6H), 4.56 (s, 1H), 5.34 (1H, d), 7.74 (d, 1H).

Workup

  1. temperatureto cool
  2. customthe volatiles removed by evaporation

Sources & evidence

ORD record
ord-a1be3a8fa3164d35b6f810b26f31e32b
Source dataset
uspto-grants-2009_08
Patent number
US07579344B2

Reaction notes

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