反応 #7982

反応方程式

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

反応条件

後処理

1. 1
   温度After cooling to room temperature
2. 2
   その他the mixture was partitioned between EtOAc (50 mL) and water (50 mL)
3. 3
   洗浄The organic phase was washed with brine (20 mL)
4. 4
   乾燥dried over MgSO4
5. 5
   ろ過filtered
6. 6
   その他evaporated under vacuum
7. 7
   その他The residue was purified by preparative layer chromatography on two 0.1×20×20 cm silica gel GF plates
8. 8
   洗浄The product bands were eluted with 10% MeOH in CH2Cl2
9. 9
   その他the eluant evaporated under vacuum

実験手順

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.

出典