3-Acetylpyridine → ethyl (2Z)-3-(pyridin-3-yl)but-2-enoate

HRID 224875

Reaction equation

HRID 224875 reaction equation
[Br-].[CH2:2]([O:4]C(C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)[CH3:3].[O-:27][CH2:28][CH3:29].[Na+].[C:31]([C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1)(=O)[CH3:32]>C(O)C>[N:36]1[CH:37]=[CH:38][CH:39]=[C:34](/[C:31](/[CH3:32])=[CH:29]\[C:28]([O:4][CH2:2][CH3:3])=[O:27])[CH:35]=1

Participants

5

Reactant 3

HCID 95893-AcetylpyridineHCID 73731(Ethoxycarbonylmethyl)triphenylphosphonium bromideHCID 2723922Sodium ethoxide

Product 1

HCID 67402107ethyl (2Z)-3-(pyridin-3-yl)but-2-enoateYield 111.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

Ethoxycarbonylmethyltriphenylphosphonium bromide (100 g) in ethanol (500 ml) was added with stirring under nitrogen to a solution of sodium ethoxide (from 4.28 g sodium) in ethanol (100 ml). 3-Acetylpyridine (18.8 g) in ethanol (300 ml) was added dropwise over 0.5 hour. The mixture was allowed to stand for 14 days and was evaporated to dryness. The residue was taken up in water, the pH adjusted to 8.5 and the mixture was extracted with benzene. The extract was dried, evaporated and the residue was distilled at reduced pressure to give ethyl 3-(3-pyridyl)-crotonate (13.39 g) b.p. 78°/0.1 mmHg.

Workup

  1. customwas evaporated to dryness
  2. extractionthe mixture was extracted with benzene
  3. customThe extract was dried
  4. customevaporated
  5. distillationthe residue was distilled at reduced pressure

Sources & evidence

ORD record
ord-e810e93309c649d99782bfc28a9990d6
Source dataset
uspto-grants-1980_11
Patent number
US04234588

Linked notes

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