Boron trifluoride etherate → HCID 18174516, compound

HRID 395700Notes

Reaction equation

HRID 395700 reaction equation
[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

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 98152811-ethoxy-1-trimethylsiloxyetheneHCID 18174424HCID 18174424, compound

Product 1

HCID 18174516HCID 18174516, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-5b7a208150d04b4daf0a5b1bde1a79bd
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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