Dimethylformamide dimethyl acetal → 3-(Dimethylaminomethylidene)-6-methylpyran-2,4-dione

HRID 359587Notes

Reaction equation

HRID 359587 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[OH:9][C:10]1[CH:15]=[C:14]([CH3:16])[O:13][C:12](=[O:17])[CH:11]=1>O1CCOCC1>[CH3:6][N:4]([CH:3]=[C:11]1[C:10](=[O:9])[CH:15]=[C:14]([CH3:16])[O:13][C:12]1=[O:17])[CH3:5]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 14897943-(Dimethylaminomethylidene)-6-methylpyran-2,4-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N,N-dimethylformamide dimethyl acetal (150 ml) is added dropwise to a mixture of 4-hydroxy-6-methyl-2-pyrone (100 g) in dioxane (400 ml) at 0° C. over 20 minutes. The mixture is warmed to room temperature and stirred an additional 4 hours. The precipitated solid is filtered, washed with isopropanol and dried to give 85.0 g of the title compound. The filtrate is concentrated and isopropanol (300 ml) is added to the residue. This mixture is kept at 0° C. overnight to give an additional 18.8 g of the title compound. Physical characteristics are as follows:

Workup

  1. filtrationThe precipitated solid is filtered
  2. washwashed with isopropanol
  3. customdried

Sources & evidence

ORD record
ord-79097b4d5088439498404c5c15965d47
Source dataset
uspto-grants-1991_03
Patent number
US05001235

Reaction notes

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