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

HRID 249081Notes

Reaction equation

HRID 249081 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-56b6c20fb270444e9bdb06a7eae2f3e7
Source dataset
uspto-grants-1993_05
Patent number
US05212314

Reaction notes

Loading…