Ethanol → Tert-butyl 6-(hydroxymethyl)pyridine-3-carboxylate

HRID 868354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 868354
[O-]CC.[Na+].[Na].C(O)C.C([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:16][N:15]=1)(=O)C>C(Cl)(Cl)Cl.O.C(O)(=O)C>[C:23]([O:22][C:20]([C:17]1[CH:18]=[CH:19][C:14]([CH2:13][OH:12])=[N:15][CH:16]=1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Komponenten

8

Edukt 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 545296935-t-Butoxycarbonyl-2-pyridylmethanol acetate

Produkt 1

HCID 21287980Tert-butyl 6-(hydroxymethyl)pyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of sodium ethoxide, prepared from 0.5 g of sodium and 12.5 ml of dry ethanol, is added to a solution of the crude 5-t-butoxycarbonyl-2-pyridylmethanol acetate in 26 ml of chloroform, and the mixture is stirred at room temperature for 2 hours. The reaction mixture is neutralized by adding a solution of 3.3 ml of acetic acid in 65 ml of water and extracted with three 70-ml portions of chloroform. The combined extracts are dried over magnesium sulfate and concentrated to give 4.1 g of 5-t-butoxycarbonyl-2-pyridylmethanol.

Aufarbeitung

  1. extractionextracted with three 70-ml portions of chloroform
  2. dry with materialThe combined extracts are dried over magnesium sulfate
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e1dc74ab0e7a418bb8e549dd853a70f4
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04778796

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