TBAF tetrahydrofuran → HCID 22929956, compound

HRID 1296009Notes

Reaction equation

HRID 1296009 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.C(C1([SiH2][C:35]([O:52]C(C2C=NC(C3CC3)=CC=2)([SiH2]C2C=CC=CC=2)[SiH2]C2(C(C)(C)C)C=CC=CC2)([C:43]2[CH:44]=[N:45][C:46]([CH:49]3[CH2:51][CH2:50]3)=[CH:47][CH:48]=2)[SiH2]C2C=CC=CC=2)C=CC=CC1)(C)(C)C>O1CCCC1>[CH:49]1([C:46]2[N:45]=[CH:44][C:43]([CH2:35][OH:52])=[CH:48][CH:47]=2)[CH2:51][CH2:50]1

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 137328929HCID 137328929, compound

Product 1

HCID 22929956HCID 22929956, compoundYield 119.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After adding 1.0 M tetra n-butylammonium fluoride-tetrahydrofuran (3.7 ml, 3.7 mmol) to a solution of 1-(tert-butyl)-1,1-diphenylsilyl [(6-cyclopropyl-3-pyridyl)methyl]ether (1.3 g) in tetrahydrofuran (7 ml) dropwise while cooling on ice, the mixture was stirred for 1 hour. After confirming completion of the reaction by thin layer chromatography, the solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (283 mg, two steps, 14%) as a colorless oil.

Workup

  1. temperaturewhile cooling on ice
  2. customcompletion of the reaction by thin layer chromatography
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-f4e5cce6bd754e84ba3dbb995d1dda5f
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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