Tetrabutylammonium Fluoride Trihydrate → {4-(Benzyloxy)-3-[(4-fluorophenyl)sulphonyl]phenyl}methanol

HRID 1836550Notes

Reaction equation

HRID 1836550 reaction equation
[CH2:1]([O:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][O:14][Si](C(C)(C)C)(C)C)=[CH:11][C:10]=1[S:24]([C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)(=[O:26])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][OH:14])=[CH:11][C:10]=1[S:24]([C:27]1[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=1)(=[O:26])=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 23499610({4-(Benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzyl}oxy)(tertbutyl)dimethylsilane

Product 1

HCID 23499600{4-(Benzyloxy)-3-[(4-fluorophenyl)sulphonyl]phenyl}methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.4 g (6.99 mmol) of ({4-(benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzyl}oxy)(tertbutyl)dimethylsilane (Example IV) are dissolved in 10 ml of tetrahydrofuran. At room temperature, 7.68 mmol of tetrabutylammonium fluoride trihydrate (1-molar solution in THF) are added. The mixture is stirred at room temperature overnight. The solvent is then removed under reduced pressure and the product is purified by chromatography on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 3:2). This gives 2.1 g (81% of theory) of {4-(benzyloxy)-3-[(4-fluorophenyl)sulphonyl]phenyl}methanol.

Workup

  1. customThe solvent is then removed under reduced pressure
  2. customthe product is purified by chromatography on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 3:2)

Sources & evidence

ORD record
ord-c8c7f73d58534247b24d15a4407f9d41
Source dataset
uspto-grants-2004_08
Patent number
US06777442B2

Reaction notes

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