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

HRID 2249233Notes

Reaction equation

HRID 2249233 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-87837acb561a42a086cab34af0bac0ca
Source dataset
uspto-grants-1991_08
Patent number
US05043449

Reaction notes

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