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

HRID 1348896Notes

Reaction equation

HRID 1348896 reaction equation
[OH:1][C:2]1[O:3][C:4]([CH3:9])=[CH:5][C:6](=[O:8])[CH:7]=1.CO[CH:12](OC)[N:13]([CH3:15])[CH3:14]>C1(C)C=CC=CC=1>[CH3:12][N:13]([CH:15]=[C:7]1[C:6](=[O:8])[CH:5]=[C:4]([CH3:9])[O:3][C:2]1=[O:1])[CH3:14]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178429102HCID 178429102, compound

Product 1

HCID 14897943-(Dimethylaminomethylidene)-6-methylpyran-2,4-dioneYield 75,340.297%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 2-hydroxy-6-methyl-4H-pyran-4-one (23.92 g, 0.189 mmol) and dimethylformamide dimethyl acetal (45.2 mL, 0.34 mmol) in toluene (100 mL) was stirred at room temperature for 4 hours and concentrated to provide 25.8 g (75%) of the desired product of sufficient purity for subsequent use. MS (DCI/NH3) m/z 182 (M+H)+; 1H NMR (CDCl3) δ 8.22 (s, 1H), 5.67 (s, 1H), 3.47 (s, 3H), 3.39 (s, 3H), 2.13 (s, 3H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-341ec480fba340f3b556c3e028033f59
Source dataset
uspto-grants-2007_05
Patent number
US07211595B2

Reaction notes

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