Aspirin → 2-Acetyloxybenzoic acid 6-(chloromethyl)-2methylpyridinyl ester

HRID 2224646Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2224646
[C:1]([O:4][C:5]1[C:6](=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].CC[O-].[Na+].[Cl:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26]Cl)[N:21]=1>CN(C=O)C.C(OCC)C>[Cl:18][CH2:19][C:20]1[N:21]=[C:22]([CH3:26])[C:23]([O:8][C:7](=[O:9])[C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[O:4][C:1](=[O:3])[CH3:2])=[CH:24][CH:25]=1

Komponenten

6

Edukt 3

HCID 2244AspirinHCID 3166542,6-Bis(chloromethyl)pyridineHCID 2723922Sodium ethoxide

Produkt 1

HCID 688807642-Acetyloxybenzoic acid 6-(chloromethyl)-2methylpyridinyl esterAusbeute 59,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of acetylsalicylic acid (1.6 g, 8.88 mmoles) in N,N′-dimethylformamide (20 ml) and under stirring, sodium ethylate (0.64 g, 8.88 mmoles) is added. After 30 minutes the obtained solution is added to a solution of 2,6-bis-(chloromethyl)pyridine (4.72 g, 26.81 mmoles) in N,N′-dimethylformamide (20 ml). The solution is left at room temperature for 7 days, under stirring, then it is diluted with ethyl ether and washed with water. The separated organic phases are anhydrified with sodium sulphate and the solvent is evaporated at reduced pressure. The reaction crude product is purified by chromatography on silica gel eluting with n-hexane/ethyl acetate 7/3. 1.7 g of the product are obtained as a yellow oil.

Aufarbeitung

  1. washwashed with water
  2. customthe solvent is evaporated at reduced pressure
  3. customThe reaction crude product
  4. customis purified by chromatography on silica gel eluting with n-hexane/ethyl acetate 7/3

Quellen und Nachweise

ORD-Eintrag
ord-be81e161db1b46a2ad3f078e9f9687cb
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07378437B2

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