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

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.

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

ORD record

ord-b0de1392b0b84d2185cf6f1d50ed2ab3

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07371747B2