Boron trifluoride etherate → HCID 18174516、化合物

HRID 427550ノート

反応式

HRID 427550 の反応式
[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

参加物

5

反応物 3

HCID 8000Boron trifluoride etherateHCID 98152811-Ethoxy-1-trimethylsiloxyetheneHCID 18174424HCID 18174424、化合物

生成物 1

HCID 18174516HCID 18174516、化合物収率 50.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6a83eacfe4ee4067be76fddb39879308
出典データセット
uspto-grants-2001_11
特許番号
US06313122B1

反応ノート

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