Boron trifluoride etherate → 1-Azido-1-methylcyclopentane

HRID 246582Notes

Reaction equation

HRID 246582 reaction equation
B(F)(F)F.CCOCC.[CH3:10][C:11]1(O)[CH2:15][CH2:14][CH2:13][CH2:12]1.C[Si]([N:21]=[N+:22]=[N-:23])(C)C>C1(C)C=CC=CC=1>[N:21]([C:11]1([CH3:10])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[N+:22]=[N-:23]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 738301-MethylcyclopentanolHCID 78378Azidotrimethylsilane

Product 1

HCID 866779941-Azido-1-methylcyclopentaneYield 110.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

BF3.Et2O (934 mg, 6.23 mmol) was added drop-wise at 20° C. to a stirred solution of 1-methylcyclopentanol (520 mg, 5.19 mmol) and trimethylsilyl azide (716 mg, 6.23 mmol) in 6 mL of toluene. Then the solution was stirred at room temperature for 16 hours. The organic phase was washed with a 10% solution of NaHCO3 (10 mL), water (5 mL) and brine (5 mL), and dried over anhydrous sodium sulfate. The drying agent was removed by filtration and the solvent was evaporated at 35° C. under reduced pressure to give 1-azido-1-methylcyclopentane (720 mg) as a crude product. It was used directly in the next step without further purification.

Workup

  1. washThe organic phase was washed with a 10% solution of NaHCO3 (10 mL), water (5 mL) and brine (5 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe drying agent was removed by filtration
  4. customthe solvent was evaporated at 35° C. under reduced pressure

Sources & evidence

ORD record
ord-a713a77f9ac642e1885baae772931151
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

Loading…