Tetrabutylammonium Fluoride → [3-(Cyclopentylsulfanyl)phenyl]methanol

HRID 2116992Notes

Reaction equation

HRID 2116992 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([Si]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([S:34][CH:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:29]=1)(C)C)(C)(C)C>C1COCC1>[CH:35]1([S:34][C:30]2[CH:29]=[C:28]([CH2:27][OH:26])[CH:33]=[CH:32][CH:31]=2)[CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66845801Tert-butyl([3-(cyclopentylthio)benzyl]oxy}dimethylsilane

Product 1

HCID 66347770[3-(Cyclopentylsulfanyl)phenyl]methanolYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tetrabutylammonium fluoride in THF (1M, 6 ml) was added to a solution of tert-butyl{[3-(cyclopentylthio)benzyl]oxy}dimethylsilane (1.09 g) in dry THF (10 ml). The solution was stirred for 18 h under nitrogen and the solvent was evaporated in vacuo. The residue was partitioned between dichloromethane and water. The organic phase was separated and washed with water. The organic phase was separated and the solvent evaporated in vacuo. The residue was purified on a 10 g silica SPE cartridge, eluting with a stepped gradient of 10% to 100% dichloromethane-cyclohexane to give the title compound (0.65 g). LCMS RT=3.3 min

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe residue was partitioned between dichloromethane and water
  3. customThe organic phase was separated
  4. washwashed with water
  5. customThe organic phase was separated
  6. customthe solvent evaporated in vacuo
  7. customThe residue was purified on a 10 g silica SPE cartridge
  8. washeluting with a stepped gradient of 10% to 100% dichloromethane-cyclohexane

Sources & evidence

ORD record
ord-92ed91061dfa415ea6f501b4d1ef5b1d
Source dataset
uspto-grants-2008_10
Patent number
US07439393B2

Reaction notes

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