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

HRID 1589268Notes

Reaction equation

HRID 1589268 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-79807a8d264f4101b312aeefa8d974b7
Source dataset
uspto-grants-1986_02
Patent number
US04568751

Reaction notes

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