4-Chloropyridine → HCID 69284462, compound

HRID 450852

Reaction equation

HRID 450852 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([O:12]CC)=O)=[CH:7][C:6]=2[CH:15]=1.Cl[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10](=[O:12])[C:22]3[CH:17]=[CH:3][CH:2]=[CH:15][C:21]=3[N:20]3[CH2:7][CH2:8][O:9][CH2:18][CH2:19]3)=[CH:7][C:6]=2[CH:15]=1

Participants

4

Reactant 2

HCID 122884-ChloropyridineHCID 2799299Ethyl 5-chlorobenzofuran-2-carboxylate

Product 1

HCID 69284462HCID 69284462, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 5-chlorobenzofuran-2-carboxylate (350 mg, 1.56 mmol) in THF (10 ml) is added at −70° C. to a THF solution of lithiated 4-chloropyridine (1.8 mmol prepared according to G. Quéguiner et al., Synthesis 1986, 886-891). The mixture is allowed to reach room temperature within 16 hours before quenching with acetic acid. The product is extracted with chloroform. Drying and chromatography on silicagel gives the title compound.

Workup

  1. custombefore quenching with acetic acid
  2. extractionThe product is extracted with chloroform
  3. customDrying

Sources & evidence

ORD record
ord-87f9061cd16240e8b1cc4d37ba8988e8
Source dataset
uspto-grants-2013_07
Patent number
US08486996B2

Linked notes

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