Реакция #7982

Уравнение реакции

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

Условия реакции

Обработка

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

Методика

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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