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

HRID 569568Notes

Reaction equation

HRID 569568 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 overnight under argon. The resulting red liquid 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 liquid 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-9d55628f5206412bb97726f994201d60
Source dataset
uspto-grants-1988_03
Patent number
US04732982

Reaction notes

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