Boron trifluoride etherate → 1-(1-Azido-4-methylene-cyclohexyl)-3-tert-butyl-benzene

HRID 132105Notes

Reaction equation

HRID 132105 reaction equation
B(F)(F)F.CCOCC.[C:10]([C:14]1[CH:15]=[C:16]([C:20]2(O)[CH2:25][CH2:24][C:23](=[CH2:26])[CH2:22][CH2:21]2)[CH:17]=[CH:18][CH:19]=1)([CH3:13])([CH3:12])[CH3:11].[N:28]([Si](C)(C)C)=[N+:29]=[N-:30].C(OCC)(=O)C>C(OCC)C.[Cl-].[NH4+]>[N:28]([C:20]1([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:15]=2)[CH2:25][CH2:24][C:23](=[CH2:26])[CH2:22][CH2:21]1)=[N+:29]=[N-:30]

Participants

7

Reactant 4

HCID 8000Boron trifluoride etherateHCID 8857Ethyl AcetateHCID 78378AzidotrimethylsilaneHCID 597337431-(3-Tert-butyl-phenyl)-4-methylene-cyclohexanol

Product 1

HCID 597337741-(1-Azido-4-methylene-cyclohexyl)-3-tert-butyl-benzeneYield 37%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Borontrifluoride-etherate (2.0 mL, 15.7 mmol) was added to a solution of 1-(3-tert-butyl-phenyl)-4-methylene-cyclohexanol (3.60 g, 14.7 mmol) and azidotrimethylsilane (4.0 mL, 30.1 mmol) in diethyl ether (30 mL) and placed into a preheated oil bath at 45° C. After heating at reflux for 4 h, the solution was diluted with saturated aqueous ammonium chloride and extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was flash chromatographed with 99:1, 49:1, and 24:1 hexanes:ethyl acetate as the eluant to yield 1.46 g (37% yield) of 1-(1-azido-4-methylene-cyclohexyl)-3-tert-butyl-benzene as a clear oil.

Workup

  1. customplaced into a preheated oil bath at 45° C
  2. temperatureAfter heating
  3. temperatureat reflux for 4 h
  4. extractionextracted with diethyl ether
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed with 99:1, 49:1, and 24:1 hexanes

Sources & evidence

ORD record
ord-c545de57703d40bdbad60b33728fa6c1
Source dataset
uspto-grants-2008_06
Patent number
US07385085B2

Reaction notes

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