반응 #7982

반응 방정식

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

반응 조건

후처리

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

실험 절차

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.

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