Реакция #7944

Уравнение реакции

2-butyl-5-methoxy-4-methyl-2-(3-oxo-butyl)-1-indanone

acetic acid

pyrrolidine

→

9a-butyl-7-methoxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Выход 55.5%

Растворители

toluene

Et2O

Условия реакции

Обработка

1. 1
   ТемператураAfter cooling
2. 2
   Промывкаwashed with 1N HCl (2×25 mL), 5% NaHCO3 (50 mL), and brine (50 mL)
3. 3
   Сушкаdried over MgSO4
4. 4
   Фильтрацияfiltered
5. 5
   Другоеevaporated under vacuum to a dark brown oil (0.86 g)
6. 6
   ДругоеThe crude product was purified by chromatography on a Biotage FLASH 40S column
7. 7
   Промывкаeluting with 9:1 hexanes-EtOAc

Методика

A solution of impure 2-butyl-5-methoxy-4-methyl-2-(3-oxo-butyl)-1-indanone (0.96 g, 3.17 mmol), acetic acid (0.182 mL, 3.18 mmol) and pyrrolidine (0.265 mL, 3.18 mmol) in anhydrous toluene (15.9 mL) was stirred and heated in an oil bath at 80° C. for 16 hours. After cooling, the reaction mixture was diluted with Et2O (100 mL), washed with 1N HCl (2×25 mL), 5% NaHCO3 (50 mL), and brine (50 mL), dried over MgSO4, filtered, and evaporated under vacuum to a dark brown oil (0.86 g). The crude product was purified by chromatography on a Biotage FLASH 40S column, eluting with 9:1 hexanes-EtOAc, to afford 9a-butyl-7-methoxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (0.50 g) as an off-white solid.

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