Carbon Dioxide → Methyl 11-methoxy-6,11-dihydrodibenz[b,e]oxepin-3-carboxylate

HRID 5044

반응식

HRID 5044 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH:11]([O:12][CH3:13])[C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[CH2:8][O:7][C:6]=2[CH:18]=1.C([Li])CCC.[CH3:24]CCCCC.[C:30](=[O:32])=[O:31].S(=O)(=O)(O)O>O1CCCC1.CO>[CH3:13][O:12][CH:11]1[C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[CH2:8][O:7][C:6]2[CH:18]=[C:2]([C:30]([O:32][CH3:24])=[O:31])[CH:3]=[CH:4][C:5]1=2

참가 물질

7

반응물 4

HCID 280Carbon DioxideHCID 1118Sulfuric AcidHCID 150931363-Bromo-11-methoxy-6,11-dihydrodibenz[b,e]oxepineHCID 178418244HCID 178418244, 화합물

생성물 1

HCID 9994021Methyl 11-methoxy-6,11-dihydrodibenz[b,e]oxepin-3-carboxylate

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

3-Bromo-11-methoxy-6,11-dihydrodibenz[b,e]oxepine, 30 g, was dissolved in 500 ml of tetrahydrofuran. After cooling to -78° C., 65 ml of 1.6 N n-butyl lithium/hexane solution was dropwise added to the solution in a nitrogen atmosphere followed by stirring at -78° C. for further 40 minutes. The reaction solution was dropwise added onto 100 g of dry ice, which was allowed to stand to elevate to room temperature. The solvent was distilled off under reduced pressure. To the residue obtained, were added 500 ml of methanol and 10 ml of conc. sulfuric acid. The mixture was heated to reflux for 2 hours. After allowing to cool, the solvent was distilled off under reduced pressure. The residue was extracted with 500 ml of ethyl acetate. After washing successively with saturated sodium chloride aqueous solution, saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution, the extract was dried over anhydrous magnesium sulfate. The solvent was the distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (eluting solvent; hexane: ethyl acetate=1:1) to give 19.3 g of the product as pale yellow oil.

후처리

  1. customto elevate to room temperature
  2. distillationThe solvent was distilled off under reduced pressure
  3. customTo the residue obtained
  4. temperatureThe mixture was heated
  5. temperatureto reflux for 2 hours
  6. temperatureto cool
  7. distillationthe solvent was distilled off under reduced pressure
  8. extractionThe residue was extracted with 500 ml of ethyl acetate
  9. washAfter washing successively with saturated sodium chloride aqueous solution, saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution
  10. dry with materialthe extract was dried over anhydrous magnesium sulfate
  11. distillationdistilled off under reduced pressure
  12. washThe residue was subjected to silica gel column chromatography (eluting solvent; hexane: ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-ba4b6bc657a14ef6912c99577adeb904
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05242931

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