Diethyl Ether → (2E)-3-(Dimethylamino)-1-(4-Pyridinyl)-2-Propen-1-One

HRID 1726387Notes

Reaction equation

HRID 1726387 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CO[CH:12](OC)[N:13]([CH3:15])[CH3:14].C(OCC)C>C1(C)C=CC=CC=1>[CH3:12][N:13]([CH3:15])/[CH:14]=[CH:2]/[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 142824-AcetylpyridineHCID 78373Dimethylformamide dimethyl acetal2×

Product 1

HCID 5396716(2E)-3-(Dimethylamino)-1-(4-Pyridinyl)-2-Propen-1-OneYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 4-acetylpyridine (23 mL) in 350 mL toluene was added 55 mL N,N-dimethylformamide dimethyl acetal. The solution was refluxed for 3 hours and allowed to stir at ambient temperature overnight. An additional 33 mL N,N-dimethylformamide dimethyl acetal of was added. After refluxing for 7 hours, the mixture was concentrated to leave an orange solid. This material was treated with diethyl ether. The resulting yellow solid was collected by vacuum filtration. A total of 25.85 g (71% yield) yellow solid was obtained. 1H NMR (CDCl3) was consistent with the desired structure. LC/MS indicated a single peak with a M+1 molecular ion of m/z 177.1 by positive ESI (electrospray ionization mass spectrometry).

Workup

  1. temperatureThe solution was refluxed for 3 hours
  2. temperatureAfter refluxing for 7 hours
  3. concentrationthe mixture was concentrated
  4. customto leave an orange solid
  5. filtrationThe resulting yellow solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-f56596d9e5de4b2a960ee7d68f2a03ea
Source dataset
uspto-grants-2009_02
Patent number
US07491829B2

Reaction notes

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