Реакция #62224

Уравнение реакции

water

30

2-Methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-one

3,4,5-trimethoxybromobenzene

n-Butyllithium

→

32

Выход 49.6%

2-Methoxy-5-(3,4,5-trimethoxyphenyl)-6,7,8,9-tetrahydro-benzocyclohepten-5-ol

Выход 49.6%

Растворители

ether

ether

Условия реакции

Обработка

1. 1
   Другоеwas brought to −78° C.
2. 2
   workup.ADDITIONwas added dropwise
3. 3
   workup.ADDITIONwas added dropwise
4. 4
   workup.STIRRINGto stir until the temperature
5. 5
   Температураwarmed up to room temperature
6. 6
   Экстракцияthe product was extracted with ether (3×50)
7. 7
   Сушкаwere dried over anhydrous magnesium sulfate
8. 8
   Фильтрацияfiltered
9. 9
   Другоеevaporated under reduced pressure
10. 10
    ДругоеPurification by column chromatography (silica gel, 20:80 EtOAc:Hexanes)

Методика

200 mL of anhydrous ether was, added to 3,4,5-trimethoxybromobenzene (1.23 g, 4.97 mmol) in a 500 mL round bottom flask under nitrogen. The temperature of the reaction mixture was brought to −78° C. n-Butyllithium (4.5 mL, 11.25 mmol) was added dropwise. The reaction mixture was then stirred until the temperature was raised gradually to −30° C. 30 (0.86 g, 4.5 mmol) dissolved in 25 mL of dry ether was added dropwise and the reaction mixture was allowed to stir until the temperature warmed up to room temperature. 25 mL of water was added and the product was extracted with ether (3×50), combined organic phases were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. Purification by column chromatography (silica gel, 20:80 EtOAc:Hexanes) yielded 800 mg (49%) of 32 as pale yellow oil Rf: 0.16 (30:70, EtOAc:Hexanes).

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