Réaction #5978

Équation de réaction

methyl 3-(3-cyclohexenyl)-4-acetylamino-5-chlorosalicylate

trifluoroacetic acid

→

methyl 1-acetylamino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate

Conditions de réaction

Traitement

1. 1
   AutreThe acid is removed under vacuum
2. 2
   workup.ADDITIONthe residue diluted with ether
3. 3
   Lavagewashed with sodium bicarbonate
4. 4
   Séchagewater, dried
5. 5
   Autreevaporated to dryness

Mode opératoire

A mixture of 1.2 g of methyl 3-(3-cyclohexenyl)-4-acetylamino-5-chlorosalicylate and 5 ml trifluoroacetic acid are stirred at room temperature overnight. The acid is removed under vacuum and the residue diluted with ether, washed with sodium bicarbonate, then water, dried and evaporated to dryness to give crude methyl 1-acetylamino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate. This product is purified by flash chromatography using 10% ethyl acetate/hexane to give pure product.

Source