Tetrabutylammonium Fluoride → 3-[5-(3-chlorophenyl)-2H-tetrazol-2-yl]butan-1-ol

HRID 639827Notes

Reaction equation

HRID 639827 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][CH2:28][CH:29]([N:31]1[N:35]=[N:34][C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=2)=[N:32]1)[CH3:30])(C(C)(C)C)(C)C>C1COCC1>[Cl:42][C:38]1[CH:37]=[C:36]([C:33]2[N:34]=[N:35][N:31]([CH:29]([CH3:30])[CH2:28][CH2:27][OH:26])[N:32]=2)[CH:41]=[CH:40][CH:39]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 684318752-(3-{[tert-butyl(dimethyl)silyl]oxy}-1-methylpropyl)-5-(3-chlorophenyl)-2H-tetrazole

Product 1

HCID 684296013-[5-(3-chlorophenyl)-2H-tetrazol-2-yl]butan-1-olYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF was added to a solution of 2-(3-{[tert-butyl(dimethyl)silyl]oxy}-1-methylpropyl)-5-(3-chlorophenyl)-2H-tetrazole in THF (25 mL). The mixture was concentrated after 4 h and the crude was purified by flash column chromatography (SiO2, Heptane-EtOAc 1:1) to give 0.90 g (91%) of the title compound.

Workup

  1. concentrationThe mixture was concentrated after 4 h
  2. customthe crude was purified by flash column chromatography (SiO2, Heptane-EtOAc 1:1)

Sources & evidence

ORD record
ord-b3459ad394b14bbaab9ff185ff823a46
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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