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

HRID 1896649Notes

Reaction equation

HRID 1896649 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[CH3:9][O:10][CH:11]([O:15][CH3:16])[C:12]([CH3:14])=[O:13]>CC(O)CC>[CH3:3][N:4]([CH3:6])/[CH:5]=[CH:14]/[C:12](=[O:13])[CH:11]([O:15][CH3:16])[O:10][CH3:9]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 80650Pyruvic aldehyde dimethyl acetal

Product 1

HCID 5709580((1E)-4,4-dimethoxy-3-oxobut-1-en-1-yl)dimethylamine

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent

Procedure

A solution of N,N-dimethylformamide dimethyl acetal (147 g, 1.23 mol) and 1,1-dimethoxyacetone (146 g, 1.24 mol) in 2-butanol (1 L) was heated at reflux for 20 hours. After removal of solvent in vacuo, the residue was distilled under vacuum to provide the product as an oil. Yield: 145 g, 0.837 mol, 68%. Boiling point: 132-140° C./0.15 torr. NMR and MS data were obtained using the product of a reaction run under similar conditions. LCMS m/z 174.0 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.77 (br s, 3H), 3.02 (br s, 3H), 3.30 (s, 6H), 4.47 (s, 1H), 5.23 (br d, J=12.6 Hz, 1H), 7.63 (d, J=12.6 Hz, 1H).

Workup

  1. temperatureat reflux for 20 hours
  2. customAfter removal of solvent in vacuo
  3. distillationthe residue was distilled under vacuum

Sources & evidence

ORD record
ord-ce62a16852ee4ee1aaed5e22282c9c07
Source dataset
uspto-grants-2013_08
Patent number
US08518944B2

Reaction notes

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