p-Toluenesulfonic acid monohydrate → HCID 117993661, compound

HRID 922574Notes

Reaction equation

HRID 922574 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10](O)([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10](=[CH2:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 101043406HCID 101043406, compound

Product 1

HCID 117993661HCID 117993661, compoundYield 179.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 2-(6-chloro-2-methoxypyridin-3-yl)-2-hydroxypropanoate (220 g, 847 mmol) and TsOH·H2O (80.5 g, 423 mmol) in dry toluene (1.5 L) was heated at reflux azeotropically with a Dean-Stark trap for 5 h. All of reaction solutions were combined together for work up. After being cooled, the combined reaction mixtures were washed with 10% Na2CO3 aq., and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated to afford ethyl 2-(6-chloro-2-methoxypyridin-3-yl)acrylate (368 g 90%) as a black oil, which was used for next step without any further purifications.

Workup

  1. temperaturewas heated
  2. temperatureat reflux azeotropically with a Dean-Stark trap for 5 h
  3. customAll of reaction solutions
  4. temperatureAfter being cooled
  5. customthe combined reaction mixtures
  6. washwere washed with 10% Na2CO3 aq.
  7. extractionthe aqueous layer was extracted with EtOAc
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-7df3a22f0cc444188cd83285e3352bac
Source dataset
uspto-grants-2016_03
Patent number
US09278953B2

Reaction notes

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