Reaktion #80303

Reaktionsgleichung

methyl 4-(acetylamino)-5-chloro-2-(2-propynoxy)benzoate

phenoxybenzene

→

methyl 5-(acetylamino)-6-chloro-2H-1-benzopyran-8-carboxylate

Ausbeute 33.8%

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   workup.ADDITIONthe reaction mixture was poured into petroleumether
3. 3
   SonstigeThe organic layer was separated
4. 4
   Sonstigedried
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 97:3)
8. 8
   SonstigeThe eluent of the desired fractions was evaporated
9. 9
   Sonstigethe residue was crystallized from acetonitrile

Vorschrift

A mixture of 40 parts of methyl 4-(acetylamino)-5-chloro-2-(2-propynoxy)benzoate and 172 parts of phenoxybenzene was stirred for 45 min. at 230° C. After cooling, the reaction mixture was poured into petroleumether. The organic layer was separated, dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 97:3). The eluent of the desired fractions was evaporated and the residue was crystallized from acetonitrile, yielding 11.9 parts (33.8%) of methyl 5-(acetylamino)-6-chloro-2H-1-benzopyran-8-carboxylate (interm. 11).

Quelle