Réaction #7982

Équation de réaction

9a-butyl-8-chloro-4-cyano-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

pyridine hydrochloride

→

9a-butyl-8-chloro-4-cyano-7-hydroxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooling to room temperature
2. 2
   Autrethe mixture was partitioned between EtOAc (50 mL) and water (50 mL)
3. 3
   LavageThe organic phase was washed with brine (20 mL)
4. 4
   Séchagedried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Autreevaporated under vacuum
7. 7
   AutreThe residue was purified by preparative layer chromatography on two 0.1×20×20 cm silica gel GF plates
8. 8
   LavageThe product bands were eluted with 10% MeOH in CH2Cl2
9. 9
   Autrethe eluant evaporated under vacuum

Mode opératoire

A mixture of 9a-butyl-8-chloro-4-cyano-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (65 mg) and pyridine hydrochloride (4.2 g) was heated in an oil bath at 200° C. for 85 minutes. After cooling to room temperature, the mixture was partitioned between EtOAc (50 mL) and water (50 mL). The organic phase was washed with brine (20 mL), dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified by preparative layer chromatography on two 0.1×20×20 cm silica gel GF plates, developing with 5% MeOH in CH2Cl2. The product bands were eluted with 10% MeOH in CH2Cl2, the eluant evaporated under vacuum, and the residue lyophilized from benzene (3 mL) plus EtOH (0.1 mL) to afford 9a-butyl-8-chloro-4-cyano-7-hydroxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an amorphous yellow solid.

Source