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Tetrahydrofuran → {4-[5-(4-Isobutylphenyl)-1,3,4-oxadiazol-2-yl]phenyl}methanol

HRID 2242236
Notes
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Reaction equation

HRID 2242236 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[O:35][C:36]([C:39]3[CH:44]=[CH:43][C:42]([CH2:45][CH:46]([CH3:48])[CH3:47])=[CH:41][CH:40]=3)=[N:37][N:38]=2)=[CH:30][CH:29]=1)(C(C)(C)C)(C)C.C1COCC1>C(OCC)(=O)C>[CH2:45]([C:42]1[CH:41]=[CH:40][C:39]([C:36]2[O:35][C:34]([C:31]3[CH:30]=[CH:29][C:28]([CH2:27][OH:26])=[CH:33][CH:32]=3)=[N:38][N:37]=2)=[CH:44][CH:43]=1)[CH:46]([CH3:48])[CH3:47]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 592042842-[4-({[Tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]-5-(4-isobutylphenyl)-1,3,4-oxadiazole

Product 1

HCID 59204276{4-[5-(4-Isobutylphenyl)-1,3,4-oxadiazol-2-yl]phenyl}methanolYield 88.5%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Procedure

Tetrabutylammonium fluoride (1.0 M in THF, 2.0 mL) was added to a solution of 2-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]-5-(4-isobutylphenyl)-1,3,4-oxadiazole (0.50 g, 1.18 mmol) and THF (10 mL) and stirred at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate (100 mL), washed with water and brine, dried (Na2SO4,), filtered and concentrated in vacuo to give the title compound (0.322 g, 88% yield) as a white solid.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4,)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b18b14a2adc740f8bcc93019f46efd5f
Source dataset
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07671043B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes