Reaktion #6137

ord-231454abe7284d98adfcccdd34ddb1a5

Reaktionsgleichung

N#Cc1ccccc1O
2-hydroxybenzonitrile
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide
→
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1C#N
expected product
Ausbeute 20.0%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1ccccc1C#N
2-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside
Ausbeute 20.0%

Edukte

N#Cc1ccccc1O
2-hydroxybenzonitrile
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide

Reagenzien

[Ag+].c1c[n-]cn1
silver imidazolate
[Cl-].[Cl-].[Zn+2]
zinc chloride

Lösungsmittel

ClCCl
methylene chloride

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeIf the procedure described in Preparation LXXXIII

Vorschrift

If the procedure described in Preparation LXXXIII is followed starting from 2 g (16.8.10-3 mol) of 2-hydroxybenzonitrile, 4.4 g (25.1.10-3 mol) of silver imidazolate, 6.5 g (18.3.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 4.6 g (33.6.10-3 mol) of zinc chloride in 80 ml of methylene chloride, 1.32 g (yield: 20%) of the expected product are obtained after purification by chromatography on silica gel using a toluene/ethyl acetate mixture (6/1 v/v) as the eluent, and precipitation in ether.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05246961uspto-grants-1993_09