Tetrabutylammonium Fluoride → 4-{4-(Benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzyl}-3,5-dimethylphenol

HRID 1836555Notes

Reaction equation

HRID 1836555 reaction equation
[CH2:1]([O:8][C:9]1[CH:34]=[CH:33][C:12]([CH2:13][C:14]2[C:30]([CH3:31])=[CH:29][C:17]([O:18][Si](C(C)C)(C(C)C)C(C)C)=[CH:16][C:15]=2[CH3:32])=[CH:11][C:10]=1[S:35]([C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=1)(=[O:37])=[O:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClC(Cl)C>[CH2:1]([O:8][C:9]1[CH:34]=[CH:33][C:12]([CH2:13][C:14]2[C:30]([CH3:31])=[CH:29][C:17]([OH:18])=[CH:16][C:15]=2[CH3:32])=[CH:11][C:10]=1[S:35]([C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=1)(=[O:36])=[O:37])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 23499604(4-{4-(Benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzyl}-3,5-dimethylphenoxy)(triisopropyl)silane

Product 1

HCID 234996174-{4-(Benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzyl}-3,5-dimethylphenol

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

600 mg (9.95 mmol) of (4-{4-(benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzyl}-3,5-dimethylphenoxy)-(triisopropyl)silane (Example IX) are dissolved in 15 ml of dichloroethane. At room temperature, 359 mg (1.14 mmol) of tetrabutylammonium fluoride are added, and the mixture is stirred for thirty minutes. The solvent is then removed under reduced pressure and the product is purified by silica gel chromatography (mobile phase cyclohexane/ethyl acetate 9:1). This gives 180 mg (40% of theory) of 4-{4-(benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzyl}-3,5-dimethylphenol.

Workup

  1. customThe solvent is then removed under reduced pressure
  2. customthe product is purified by silica gel chromatography (mobile phase cyclohexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-a20c0f5bd5a043ed806a7f27710858db
Source dataset
uspto-grants-2004_08
Patent number
US06777442B2

Reaction notes

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