Reaktion #94682

Reaktionsgleichung

4-hydroxy-1-iodo-trans-1-octene

pyridinium chlorochromate

sodium acetate

→

4-Oxo-1-iodo-trans-1-octene

Lösungsmittel

methylene chloride

ether

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedecanted
2. 2
   WaschenThe solid sludge is washed repeatedly with ether
3. 3
   Sonstigedecanted
4. 4
   EinengenThe solution is concentrated

Vorschrift

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).

Quelle