Ethyl Acetate → (4-Triisopropylsilanylsulfanyl-phenyl)-methanol

HRID 2222941Notes

Reaction equation

HRID 2222941 reaction equation
[CH:1]([Si:4]([SH:11])([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[H-].[K+].Br[C:15]1[CH:22]=[CH:21][C:18]([CH2:19][OH:20])=[CH:17][CH:16]=1.C(OCC)(=O)C>O1CCCC1.C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH:1]([Si:4]([S:11][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][OH:20])=[CH:17][CH:16]=1)([CH:5]([CH3:7])[CH3:6])[CH:8]([CH3:10])[CH3:9])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 701194-Bromobenzyl alcoholHCID 82127Potassium hydrideHCID 3435097Tris(propan-2-yl)silanethiol

Product 1

HCID 69114972(4-Triisopropylsilanylsulfanyl-phenyl)-methanol

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of triisopropylsilyl thiol (1.904 g, 10.0 mmol) in tetrahydrofuran (10 mL) was added to a stirred suspension of potassium hydride in tetrahydrofuran (10 mL). The resulting suspension was then added to a stirred solution of 4-bromobenzyl alcohol (1.87 g, 10 mmol) and tetrakis[triphenylphosphine]palladium(0) (0.350 g, 0.30 mmol) in benzene (25 mL). The reaction mixture was stirred at reflux for 2 h under a nitrogen atmosphere. Ethyl acetate (200 mL) was added and the solution washed with water. The organic phase was dried with magnesium sulfate, filtered, and concentrated by rotary evaporation. The crude product was purified by silica gel chromatography using a gradient of 0% to 2% ethyl acetate in dichloromethane to yield (4-triisopropylsilanylsulfanyl-phenyl)-methanol as a colorless oil.

Workup

  1. temperatureat reflux for 2 h under a nitrogen atmosphere
  2. washthe solution washed with water
  3. dry with materialThe organic phase was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b0de1392b0b84d2185cf6f1d50ed2ab3
Source dataset
uspto-grants-2008_05
Patent number
US07371747B2

Reaction notes

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