Реакция #1680830

Уравнение реакции

NaOH

(6aR,10aS)-2-fluoro-9-methoxy-6a-nitro-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-6-one

H2SO4

→

product

Выход 19.1%

8-fluoro-3,4-dihydrodibenzo[b,d]furan-2(1H)-one

Выход 19.1%

Растворители

H2O

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas rapidly added to the alkaline solution
2. 2
   workup.WAITleft
3. 3
   Температураalso cooled to 0° C
4. 4
   workup.WAITThe mixture was left
5. 5
   workup.STIRRINGstirring at 0° C. for 5 min
6. 6
   workup.STIRRINGto stir at RT for 1 h
7. 7
   Экстракцияsaturated with brine, and extracted with EtOAc
8. 8
   СушкаThe organic layer was then dried over anhydrous Na2SO4
9. 9
   Концентрированиеconcentrated under reduced pressure
10. 10
    ДругоеPurification by flash chromatography on silica gel

Методика

To a 250 mL flask were added CTABr (0.933 g, 2.56 mmol), NaOH (23.04 g, 576 mmol), and H2O (100 mL), and the resulting solution was warmed to 50° C. (6aR,10aS)-2-fluoro-9-methoxy-6a-nitro-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-6-one (3.75 g, 12.80 mmol) was rapidly added to the alkaline solution and left under stirring for 1 h. The green solution was then cooled to 0° C., and added dropwise to a solution of H2SO4 (3.75 M, 100 mL) also cooled to 0° C. The mixture was left stirring at 0° C. for 5 min, and was then allowed to stir at RT for 1 h. The mixture was then saturated with brine, and extracted with EtOAc. The organic layer was then dried over anhydrous Na2SO4, and concentrated under reduced pressure. Purification by flash chromatography on silica gel afforded the product as a white solid (0.50 g, 19%); MS (EI) m/z=204 [M+].

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