Ethanol → (E)-ethyl 2-acetamido-3-(dimethylamino)but-2-enoate

HRID 75494

Reaction equation

HRID 75494 reaction equation
[CH3:1][N:2]([CH3:12])/[C:3](=[C:5]1/[N:6]=[C:7]([CH3:11])[O:8][C:9]/1=[O:10])/[CH3:4].[H-].[Na+].[CH2:15]([OH:17])[CH3:16]>>[C:15]([NH:6]/[C:5](=[C:3](/[N:2]([CH3:12])[CH3:1])\[CH3:4])/[C:9]([O:8][CH2:7][CH3:11])=[O:10])(=[O:17])[CH3:16]

Participants

4

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 21985397(E)-4-(1-(dimethylamino)ethylidene)-2-methyloxazol-5(4H)-one2×

Product 1

HCID 54579441(E)-ethyl 2-acetamido-3-(dimethylamino)but-2-enoate

Procedure

4-[1-dimethylamino-eth-(Z)-ylidene]-2-methyl-4H-oxazole-5-one (compound 15, 7.54 g, 44.8 mmol) was dissolved in ethanol (50 mL) and sodium hydride (179 mg, 4.5 mmol, 60% dispersion in mineral oil) wad added at room temperature. The solution was refluxed for 1 hr. The solvent was evaporated and the crude product was used without any further purification for the next step.

Workup

  1. temperatureThe solution was refluxed for 1 hr
  2. customThe solvent was evaporated
  3. customthe crude product was used without any further purification for the next step

Sources & evidence

ORD record
ord-05e04b54a61043f28d14b22210ba2a75
Source dataset
uspto-grants-2014_09
Patent number
US08835436B2

Linked notes

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