Dimethylformamide dimethyl acetal → 3-[(Dimethylamino)Methylene]-2,4-Octanedione

HRID 249089Notes

Reaction equation

HRID 249089 reaction equation
[CH3:1][C:2](=[O:10])[CH2:3][C:4](=[O:9])[CH2:5][CH2:6][CH2:7][CH3:8].CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>>[CH3:13][N:14]([CH:16]=[C:3]([C:4](=[O:9])[CH2:5][CH2:6][CH2:7][CH3:8])[C:2](=[O:10])[CH3:1])[CH3:15]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 841922,4-Octanedione

Product 1

HCID 544064793-[(Dimethylamino)Methylene]-2,4-Octanedione

Procedure

A mixture of 2,4-octanedione (7.11 g, 0.50 mole) and dimethylformamide dimethylacetal (7.15 g, 0.60 mole) was stirred overnight at room temperature under argon. The resulting red oil was concentrated on the rotary evaporation then distilled on the kugelrohr at -15 mm, 140°-155° C. to yield 8.60 g (87%) of 3-[(dimethylamino)methyleno]-2,4-octanodione.

Workup

  1. concentrationThe resulting red oil was concentrated on the rotary evaporation
  2. distillationthen distilled on the kugelrohr at -15 mm, 140°-155° C.
  3. customto yield 8.60 g (87%) of 3-[(dimethylamino)methyleno]-2,4-octanodione

Sources & evidence

ORD record
ord-4655d936729045fca89af9faef6a7fc7
Source dataset
uspto-grants-1993_05
Patent number
US05212315

Reaction notes

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