Benzyl Chloride → Methyl beta-D-glucopyranoside

HRID 1707728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1707728
[CH3:1][O:2][C@H:3]1[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@H:5]([OH:12])[C@H:4]1[OH:13].[H-].[Na+].C(Cl)C1C=CC=CC=1>>[CH3:1][O:2][C@@H:3]1[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@H:5]([OH:12])[C@H:4]1[OH:13]

Komponenten

4

Edukt 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 64947methyl alpha-D-glucopyranoside

Produkt 1

HCID 445238Methyl beta-D-glucopyranosideAusbeute 148,1 %

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

A general procedure according to S. Koto et al. (Bull. Chem. Soc. Japan, (1976), 49:2939-40) was followed. A suspension of methyl-α-D-glucopyranoside (Aldrich, 5.02 g, 0.0259 mol), sodium hydride (Aldrich, 4.31 g, 0.1796 mol) and benzyl chloride (Aldrich, 125 ml, 25:1 (v/w) vs carbohydrate) was stirred vigorously and heated to a bath temperature of 115° C. whereupon the gray reaction mixture thickened and an exotherm occurred. The reaction mixture reached 135° C. and turned into a thin, yellowish slurry. The reaction was allowed to stir at this temperature for 1 h. The insoluble material was removed by filtration and the solution concentrated in vacuo. Flash chromatography on silica gel (E. M. Science, 230-400 mesh) using methylene chloride as eluant gave the product (Rf value: 0.63) as an oil (7.45 g, 52%). 1H NMR data (CDCl3): δ7.27 (m, 20H, aromatic H on benzyl group), 3.45 (s, 3H, --OCH3 ).

Aufarbeitung

  1. customreached 135° C.
  2. stirringto stir at this temperature for 1 h
  3. customThe insoluble material was removed by filtration
  4. concentrationthe solution concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-38c8475264974a3dbb6030bb61abcad2
Quelldatensatz
uspto-grants-1994_10
Patentnummer
US05354853

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