Réaction #94682

ord-68eca472d9394a88a2d52e2ae26f6780

Équation de réaction

CCCCC(O)C/C=C/I
4-hydroxy-1-iodo-trans-1-octene
[O]=[Cr](=[O])([O-])[Cl].c1cc[nH+]cc1
pyridinium chlorochromate
CC(=O)[O-].[Na+]
sodium acetate
→
CCCCC(=O)C/C=C/I
4-Oxo-1-iodo-trans-1-octene

Réactifs

CCCCC(O)C/C=C/I
4-hydroxy-1-iodo-trans-1-octene
[O]=[Cr](=[O])([O-])[Cl].c1cc[nH+]cc1
pyridinium chlorochromate
CC(=O)[O-].[Na+]
sodium acetate

Réactifs

Aucun

Solvants

ClCCl
methylene chloride
CCOCC
ether
ClCCl
methylene chloride

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autredecanted
  2. 2
    LavageThe solid sludge is washed repeatedly with ether
  3. 3
    Autredecanted
  4. 4
    ConcentrationThe solution is concentrated

Mode opératoire

To a stirred suspension of 6.15 g of pyridinium chlorochromate (Tetrahedron Letters, 1975, 2647) in 20 ml of methylene chloride is added 450 mg of sodium acetate. After 5 minutes a solution of 3.64 g of 4-hydroxy-1-iodo-trans-1-octene in 15 ml of methylene chloride is added in one portion. The dark mixture is stirred at room temperature for 75 minutes, diluted with 50 ml of ether, and decanted. The solid sludge is washed repeatedly with ether and decanted. The combined solutions are percolated through Florisil. The solution is concentrated to given an orange liquid, pmr spectrum (CDCl3): 3.20 (d, j = 7 cps, =CHCH2CO).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04131737uspto-grants-1978_12