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

HRID 527334Notes

Reaction equation

HRID 527334 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[CH:3]=1.CO[CH:12](OC)[N:13]([CH3:15])[CH3:14]>C1(C)C=CC=CC=1>[CH3:12][N:13]([CH:15]=[C:3]1[C:2](=[O:1])[CH:7]=[C:6]([CH3:8])[O:5][C:4]1=[O:9])[CH3:14]

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 1140TolueneSolvent

Procedure

To a solution of 4-hydroxy-6-methyl-2-pyrone (11.50 g, 91.2 mmol) in toluene (30 mL) is added N,N-dimethylformamide dimethyl acetal (13.00 mL, 97.9 mmol). After stirring for 2 h at room temperature, the reaction mixture is evaporated under reduced pressure and co-evaporated with toluene several times. Yield: 18.5 g; ESI mass spectrum: [M+H]+=182; r.t. HPLC: 0.72 min (Z002_007).

Workup

  1. customthe reaction mixture is evaporated under reduced pressure and co-evaporated with toluene several times
  2. customr.t
  3. custom0.72 min (Z002_007)

Sources & evidence

ORD record
ord-b7126d70a19c4428a63c0b31a07bdbb5
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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