Benzyl Alcohol → Benzyl 2-iodopyridine-5-carboxylate

HRID 1073917Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1073917
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][N:3]=1.[CH2:11](O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CN(C)C1C=CN=CC=1>[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[CH:4][N:3]=1

Komponenten

6

Edukt 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 8190626-Iodopyridine-3-carboxylic acid

Produkt 1

HCID 19895696Benzyl 2-iodopyridine-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

11 g of 2-iodopyridine-5-carboxylic acid were suspended in 300 ml of dichloromethane and 4 8 g of benzyl alcohol, 10 g of dicyclohexylcarbodiimide and 100 mg of 4-dimethylaminopyridine were added. The mixture was stirred at room temperature and, after 2 hours, filtered. The filtrate was evaporated and the residue was chromatographed on silica gel using firstly ethyl acetate/petroleum ether (1:9) and then ethyl acetate/petroleum ether (1:6) for the elution. There were obtained 12.2 g of benzyl 2-iodopyridine-5-carboxylate which was used without further purification.

Aufarbeitung

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. customthe residue was chromatographed on silica gel using firstly ethyl acetate/petroleum ether (1:9)
  4. washethyl acetate/petroleum ether (1:6) for the elution

Quellen und Nachweise

ORD-Eintrag
ord-c47b90a7c8914c9ba406aa6f205d9b5b
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04971982

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