Sodium Chloride → Methyl 6-(hydroxymethyl)picolinate

HRID 744180

Reaktionsgleichung

Reaktionsgleichung von HRID 744180
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11](C2C=CC=CC=2)(C2C=CC=CC=2)[O:12][SiH2]C(C)(C)C)[N:6]=1)=[O:4].CCCC[N+](CCCC)(CCCC)CCCC.O.O.O.[F-].[Cl-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][OH:12])[N:6]=1)=[O:4]

Komponenten

5

Edukt 3

HCID 5234Sodium ChlorideHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 131719562HCID 131719562, Verbindung

Produkt 1

HCID 11513809Methyl 6-(hydroxymethyl)picolinateAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3.52 g of 6-(diphenyl-tert-butylsilyloxymethyl)-2-pyridinecarboxylic acid methyl ester in 87 ml of tetrahydrofuran is mixed at 24° C. under nitrogen with 13.6 g of tetrabutylammonium fluoride-trihydrate and stirred for 2 hours. Then, it is mixed with 32 ml of concentrated sodium chloride solution and extracted four times with ethyl acetate. The combined organic phases are dried on sodium sulfate and after filtration, concentrated by evaporation in a vacuum. The thus obtained residue is purified by chromatography on silica gel. With hexane/50-100% ethyl acetate, 0.92 g of the title compound is obtained as colorless oil.

Aufarbeitung

  1. extractionextracted four times with ethyl acetate
  2. customThe combined organic phases are dried on sodium sulfate
  3. filtrationafter filtration
  4. concentrationconcentrated by evaporation in a vacuum
  5. customThe thus obtained residue is purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-bfa52026e7254c26b24c3bde7aea5814
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05559134

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