2-Acetyl-5-Methylfuran → 3-(Dimethylamino)-1-(5-methylfuran-2-yl)prop-2-en-1-one

HRID 2352165Notes

Reaction equation

HRID 2352165 reaction equation
[C:1]([C:4]1[O:5][C:6]([CH3:9])=[CH:7][CH:8]=1)(=[O:3])[CH3:2].CO[CH:12](OC)[N:13]([CH3:15])[CH3:14]>>[CH3:12][N:13]([CH3:15])[CH:14]=[CH:2][C:1]([C:4]1[O:5][C:6]([CH3:9])=[CH:7][CH:8]=1)=[O:3]

Participants

3

Reactant 2

HCID 145142-Acetyl-5-MethylfuranHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 27670853-(Dimethylamino)-1-(5-methylfuran-2-yl)prop-2-en-1-one

Procedure

A mixture of 37.24 g of 2-acetyl-5-methylfuran and 150 ml of N,N-dimethylformamide dimethylacetal was heated on a steam bath under an air condenser for 16.5 hours. The solvent was removed in vacuo and the residue taken up in dichloromethane and passed through a short column of magnesium silicate. The filtrate was evaporated on a steam bath with the addition of n-hexanes to a volume of 100-150 ml. Cooling with scratching gave 28.31 g of the desired compound, mp 123°-125° C.

Workup

  1. temperaturewas heated on a steam bath under an air condenser for 16.5 hours
  2. customThe solvent was removed in vacuo
  3. customThe filtrate was evaporated on a steam bath with the addition of n-hexanes to a volume of 100-150 ml
  4. temperatureCooling

Sources & evidence

ORD record
ord-b20d2ece5ac4425485e460820973e90f
Source dataset
uspto-grants-1989_10
Patent number
US04876252

Reaction notes

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