Boron trifluoride etherate → HCID 178450443, compound

HRID 1067700Notes

Reaction equation

HRID 1067700 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][OH:15])[N:10]=[CH:9]2)C=CC=CC=1.ClC(Cl)(Cl)C(=N)O[C:32]([CH3:35])([CH3:34])[CH3:33].B(F)(F)F.CCOCC>C1CCCCC1.ClCCl>[NH:8]1[CH:12]=[C:11]([CH2:13][CH2:14][O:15][C:32]([CH3:35])([CH3:34])[CH3:33])[N:10]=[CH:9]1

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 2734700Tert-butyl 2,2,2-trichloroethanimidateHCID 106894902-(1-Trityl-1H-imidazol-4-yl)ethanol

Product 1

HCID 178450443HCID 178450443, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
65 °C

Procedure

2 mmol of 2-(1-triphenylmethyl-1H-imidazol-4-yl)ethanol and 4 mmol of tert-butyl trichloroacetimidate are dissolved in 4 ml of cyclohexane and 2 ml of dichloromethane. After the addition of 120 μl of boron trifluoride etherate, the solution is stirred at 60-70° C. for 18 hours. Filtration of the reaction mixture and evaporation of the solvent are followed by a detritylation in 2 ml of ethanol, 2 ml of acetone and 15 ml of 2N HCl at 70° C. The ethanol and acetone are removed under reduced pressure and triphenylmethanol is extracted with diethyl ether. The aqueous layer is alkalized with ammonia and extracted with diethyl ether. Evaporation of the solvent and final purification by column chromatography (eluent: dichloromethane/methanol, 90:10) yield the product in the form of an oil, which is crystallized in the form of the hydrogen oxalate in ethanol and diethyl ether.

Workup

  1. filtrationFiltration of the reaction mixture and evaporation of the solvent
  2. customat 70° C
  3. customThe ethanol and acetone are removed under reduced pressure and triphenylmethanol
  4. extractionis extracted with diethyl ether
  5. extractionextracted with diethyl ether
  6. customEvaporation of the solvent
  7. customfinal purification by column chromatography (eluent: dichloromethane/methanol, 90:10)
  8. customyield the product in the form of an oil, which
  9. customis crystallized in the form of the hydrogen oxalate in ethanol and diethyl ether

Sources & evidence

ORD record
ord-aa40a2755a3d400e8479628ce3fac715
Source dataset
uspto-grants-2001_06
Patent number
US06248765B1

Reaction notes

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