Boron trifluoride etherate → HCID 18794786, compound

HRID 362287Notes

Reaction equation

HRID 362287 reaction equation
C[Si]([C:5]#[N:6])(C)C.CO[CH:9]([O:28][CH3:29])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]([CH3:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:13][CH:12]=1.B(F)(F)F.CCOCC>ClCCl>[CH3:29][O:28][CH:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][N:20]([CH3:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:15][CH:16]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherate2×HCID 82115Trimethylsilyl cyanideHCID 18794822HCID 18794822, compound

Product 1

HCID 18794786HCID 18794786, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trimethylsilyl cyanide (3.4 mL) was added dropwise to a solution of 1,1-dimethoxy-2-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]phenyl]ethane (2.64 g) in dichloromethane (70 mL) at room temperature. The mixture was stirred during the addition of boron trifluoride etherate (0.3 mL), and stirring continued at room temperature for 1.5 hrs. prior to the addition of a further portion of boron trifluoride etherate (1 mL). After a further 2 hours the mixture was diluted with dichloromethane (100 mL) and washed with saturated sodium bicarbonate solution (2×300 mL), water (2×300 mL) and brine (300 mL), dried (MgSO4) and evaporated. The residue was chromatographed on silica gel with 1% methanol in dichloromethane as eluent to afford the title compound, a gum, which was used without further purification.

Workup

  1. washwashed with saturated sodium bicarbonate solution (2×300 mL), water (2×300 mL) and brine (300 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was chromatographed on silica gel with 1% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-ffa48a9bc9774bbe9bcf8835ec13acda
Source dataset
uspto-grants-1999_02
Patent number
US05869495

Reaction notes

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