Sodium Acetate → 4-Oxo-1-iodo-trans-1-octene

Participants

Reaction Steps

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 give an orange liquid, pmr spectrum (CDCl3): 3.20 (d, j=7 cps, =CHCH2CO).

Provenance & Evidence