Triethylamine → alpha-(n-Octylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide

HRID 850254

Reaktionsgleichung

Reaktionsgleichung von HRID 850254
[OH:1][N:2]=[C:3]([C:14]#[N:15])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1.[CH2:16]([S:24](Cl)(=[O:26])=[O:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(N(CC)CC)C>C(#N)C>[CH2:16]([S:24]([O:1][N:2]=[C:3]([C:14]#[N:15])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1)(=[O:26])=[O:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 822611-Octanesulfonyl chlorideHCID 86583917alpha-Hydroxyimino-3,4-dimethoxybenzyl cyanide

Produkt 1

HCID 54026326alpha-(n-Octylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

As described under 1.2, 10.3 g (0.05 mol) of α-hydroxyimino-3,4-dimethoxybenzyl cyanide are reacted with 11.7 g (0.055 mol) of 1-octanesulfonyl chloride in the presence of triethylamine. After recrystallisation of the crude product from ethyl acetate/hexane, 19.1 g (87%) of α-(n-octylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide are obtained in the form of beige crystals having a melting point of 72-75° C. The 1H-NMR spectrum of the compound shows that it is a pure stereoisomer. The UV spectrum (acetonitrile) of the substance shows a broad absorption band with a maximum at 349 nm (ε=11330) that extends to 435 nm. Elemental analysis: C18H26N2O5S (382.48)

Aufarbeitung

  1. customAfter recrystallisation of the crude product from ethyl acetate/hexane, 19.1 g (87%) of α-(n-octylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide
  2. customare obtained in the form of beige crystals

Quellen und Nachweise

ORD-Eintrag
ord-99a92c62608a43c1878cb07863b154c1
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06017675

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