Dimethylformamide diethylacetal → 3-(Dimethylamino)-2-pyridin-3-yl-acrylic acid ethyl ester

HRID 37884

Reaction equation

HRID 37884 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:2]=1.C(O[CH:16](OCC)[N:17]([CH3:19])[CH3:18])C>>[CH3:16][N:17]([CH3:19])[CH:18]=[C:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

3

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 96490Ethyl 3-pyridylacetate

Product 1

HCID 687048643-(Dimethylamino)-2-pyridin-3-yl-acrylic acid ethyl ester

Procedure

37.4 g (226 mmol) of ethyl pyridin-3-ylacetate in 100 g (679 mmol) of dimethylformamide diethyl acetal are heated at 100° C. overnight. After cooling, the mixture is concentrated and the residue is initially pre-purified by flash chromatography on silica gel (mobile phase: gradient cyclohexane/ethyl acetate 1:1 ethyl acetate/ethanol 9:1). The product obtained in this manner is then subjected to fine purification by distillation under reduced pressure (1 mbar, bath temperature 200° C.).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated
  3. customthe residue is initially pre-purified by flash chromatography on silica gel (mobile phase: gradient cyclohexane/ethyl acetate 1:1 ethyl acetate/ethanol 9:1)
  4. customThe product obtained in this manner
  5. distillationis then subjected to fine purification by distillation under reduced pressure (1 mbar, bath temperature 200° C.)

Sources & evidence

ORD record
ord-2fab76d5241947dead68d408eaf254c6
Source dataset
uspto-grants-2013_09
Patent number
US08524699B2

Linked notes

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