반응 #62224

반응 방정식

water

30

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

3,4,5-trimethoxybromobenzene

n-Butyllithium

→

32

수율 49.6%

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

수율 49.6%

용매

ether

ether

반응 조건

후처리

1. 1
   기타was 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
   온도warmed up to room temperature
6. 6
   추출the product was extracted with ether (3×50)
7. 7
   건조were dried over anhydrous magnesium sulfate
8. 8
   여과filtered
9. 9
   기타evaporated under reduced pressure
10. 10
    기타Purification by column chromatography (silica gel, 20:80 EtOAc:Hexanes)

실험 절차

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).

출처