Benzyl Bromide → 1-Benzyl-7-methoxy-3,4-dihydronaphthalen-2(1H)-one

HRID 82861

반응식

HRID 82861 반응식
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[CH2:10]2)=[CH:5][CH:4]=1.N1CCCC1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO.CO.C(Cl)Cl.O.C(O)(=O)C>[CH2:19]([CH:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[CH2:7][CH2:8][C:9]1=[O:13])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

7

반응물 3

HCID 7498Benzyl BromideHCID 31268PyrrolidineHCID 777857-Methoxy-2-tetralone

생성물 1

HCID 214101101-Benzyl-7-methoxy-3,4-dihydronaphthalen-2(1H)-one수율 95%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 21958822Dichloromethane methanol water용매

반응 조건

온도
-5 °C

실험 절차

7-methoxy-3,4-dihydronaphthalen-2(1H)-one (41 g, 233 mmol) was dissolved in MeOH (250 mL). Then pyrrolidine (18.2 g, 256 mmol) was added dropwise. The mixture was stirred for 2 h. The solvent was removed under reduced pressure and the residue was dissolved in acetonitrile (500 mL). The solution was cooled to −5° C. and benzyl bromide (43.8 g, 256 mmol) was added. The solution was stirred overnight at room temperature. The solvent was reduced under reduced pressure. The residue was dissolved in 480 mL of a mixture of MeOH/CH2Cl2/H2O (1:1:1) and 30 mL of glacial acetic acid were added. The mixture was stirred overnight. The reaction mixture was put on ice water and extracted with CH2Cl2. The combined organic layers were washed with a NaHCO3 solution and with brine. The organic phase was dried on MgSO4 and the solvent was evaporated. The residue (80 g) was purified by flash-chromatography on silica gel (100% dichloromethane). 58.8 g (221 mmol, 95%) of the product were obtained.

후처리

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in acetonitrile (500 mL)
  3. stirringThe solution was stirred overnight at room temperature
  4. additionwere added
  5. stirringThe mixture was stirred overnight
  6. extractionextracted with CH2Cl2
  7. washThe combined organic layers were washed with a NaHCO3 solution and with brine
  8. customThe organic phase was dried on MgSO4
  9. customthe solvent was evaporated
  10. customThe residue (80 g) was purified by flash-chromatography on silica gel (100% dichloromethane)

출처 및 근거

ORD 기록
ord-80508fa05c1a475b97f01929ce86441f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846741B2

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