Ethyl orthoformate → Ethyl 2-(2,6-dichloropyridine-3-carbonyl)-3-ethoxyprop-2-enoate

HRID 600864Notes

Reaction equation

HRID 600864 reaction equation
[Cl:1][C:2]1[N:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:3]=1[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[CH:17](OCC)(OCC)[O:18][CH2:19][CH3:20]>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[N:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:3]=1[C:4]([C:6](=[CH:17][O:18][CH2:19][CH3:20])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 44140080Ethyl 3-(2,6-dichloropyridin-3-YL)-3-oxopropanoate

Product 1

HCID 54146668Ethyl 2-(2,6-dichloropyridine-3-carbonyl)-3-ethoxyprop-2-enoate

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
140 °C

Procedure

Ethyl 2-(2,6-dichloronicotinoyl)acetate (7.03 g, 26.8 mmol) was dissolved in acetic anhydride (30 ml), and after adding triethyl orthoformate (60 ml) thereto, it was stirred in an oil bath of 140° C. for 2 hours. After letting the reaction solution cool, it was concentrated under a reduced pressure, and after adding toluene (50 ml) to the residue obtained, a concentration operation under a reduced pressure was performed. This operation was repeated 3 times, and the residue obtained was dried under a reduced pressure. 8.42 g of ethyl 2-(2,6-dichloronicotinoyl)-3-ethoxyacrylate was thereby obtained in the form of a yellow oily substance.

Workup

  1. temperaturecool
  2. concentrationit was concentrated under a reduced pressure
  3. additionafter adding toluene (50 ml) to the residue
  4. customobtained
  5. customthe residue obtained
  6. customwas dried under a reduced pressure

Sources & evidence

ORD record
ord-d15d8e2a789749cc9db4bfc91efb598f
Source dataset
uspto-grants-2011_03
Patent number
US07902226B2

Reaction notes

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