Boron trifluoride etherate → HCID 18174516, 화합물

HRID 395700노트

반응식

HRID 395700 반응식
[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:16]2[CH:24](OCC)[C:23]3[CH:22]=[C:21]4[CH:28]=[CH:29][CH:30]=[CH:31][C:20]4=[CH:19][C:18]=3[C:17]2=[O:32])=[O:8])=[CH:5][CH:4]=1.[CH2:35]([O:37][C:38]([O:40][Si](C)(C)C)=[CH2:39])[CH3:36].B(F)(F)F.CCOCC>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:16]2[CH:24]([CH2:39][C:38]([O:37][CH2:35][CH3:36])=[O:40])[C:23]3[CH:22]=[C:21]4[CH:28]=[CH:29][CH:30]=[CH:31][C:20]4=[CH:19][C:18]=3[C:17]2=[O:32])=[O:8])=[CH:33][CH:34]=1

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 98152811-Ethoxy-1-trimethylsiloxyetheneHCID 18174424HCID 18174424, 화합물

생성물 1

HCID 18174516HCID 18174516, 화합물수율 50.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of N-(4-methoxybenzoyl)-2-(1-ethoxy-1,3-dihydro-3-oxo-2H-benz [f]isoindol-2-yl)benzeneamine (0.75 g, 1.7 mmol) and 1-ethoxy-1-trimethylsilyloxyethylene (0.80 g, 5.0 mmol) in methylene chloride at −78° C. was treated dropwise with boron triflouride etherate (0.23 mL, 1.8 mmol). Upon complete addition, the cooling bath was removed and the mixture was allowed to warm for 0.5 h. The mixture was poured into a mixture of ethyl acetate and aqueous saturated sodium bicarbonate solution. The organic layer was washed with water, saturated sodium chloride solution, dried (potassium carbonate), and filtered. Concentration and purification of the residue by radial chromatography (silica gel, hexanes/ethyl acetate) yielded 428 mg (44%) of the title compound. An analytical sample was obtained by recrystallization from ethyl acetate/hexanes.

후처리

  1. additionUpon complete addition
  2. customthe cooling bath was removed
  3. temperatureto warm for 0.5 h
  4. additionThe mixture was poured into a mixture of ethyl acetate and aqueous saturated sodium bicarbonate solution
  5. washThe organic layer was washed with water, saturated sodium chloride solution
  6. dry with materialdried (potassium carbonate)
  7. filtrationfiltered
  8. concentrationConcentration and purification of the residue by radial chromatography (silica gel, hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-5b7a208150d04b4daf0a5b1bde1a79bd
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06605626B2

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