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

HRID 33946

반응식

HRID 33946 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5](Br)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C([Li])CCC.[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]2[C:30](=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=2[CH:32]=1.O>CCOCC>[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]2[C:30]([C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=3)([OH:31])[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=2[CH:32]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 758855-Bromo-1,2,3-trimethoxybenzeneHCID 2668152-Methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-oneHCID 178418339Butyllithium

생성물 1

HCID 689233112-Methoxy-5-(3,4,5-trimethoxyphenyl)-6,7,8,9-tetrahydro-benzocyclohepten-5-ol수율 49.6%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
-30 °C

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).

후처리

  1. customwas brought to −78° C.
  2. additionwas added dropwise
  3. additionwas added dropwise
  4. stirringto stir until the temperature
  5. temperaturewarmed up to room temperature
  6. extractionthe product was extracted with ether (3×50)
  7. dry with materialwere dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customPurification by column chromatography (silica gel, 20:80 EtOAc:Hexanes)

출처 및 근거

ORD 기록
ord-f569a7b8886a4bcea5c27723d368f13a
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429681B2

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