Reaktion #1845657

ord-4aa93656811145dfa786947a2e676a31

Reaktionsgleichung

[O]=[Cr](=[O])([O-])[O][Cr](=[O])(=[O])[O-].c1cc[nH+]cc1.c1cc[nH+]cc1
Pyridinium dichromate
CC(C)(C)OC(=O)NCCCCCCO
t-butyl-(6-hydroxyhexyl)carbamate
→
CC(C)(C)OC(=O)NCCCCCC=O
t-butyl-(5-formylpentyl)carbamate
Ausbeute 80.0%

Edukte

[O]=[Cr](=[O])([O-])[O][Cr](=[O])(=[O])[O-].c1cc[nH+]cc1.c1cc[nH+]cc1
Pyridinium dichromate
CC(C)(C)OC(=O)NCCCCCCO
t-butyl-(6-hydroxyhexyl)carbamate

Reagenzien

Keine

Lösungsmittel

CCCCC.CCOCC
diethylether pentane
ClCCl
dichloromethane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationfiltered through Florisil
  2. 2
    Einengenconcentrated

Vorschrift

Pyridinium dichromate (13.5 g, 0.036 mol) is added to a solution of t-butyl-(6-hydroxyhexyl)carbamate (5.88 g, 24 mmol) in dichloromethane (40 ml). After stirring for 24 hours, the reaction mixture is diluted with diethylether/pentane (1:1), filtered through Florisil and concentrated to yield t-butyl-(5-formylpentyl)carbamate (4.13 g, 80%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04374128uspto-grants-1983_02