Water → (3-Chlorothiophen-2-yl)trimethylsilane

Temperature

0 °C

The title compound was prepared according to the procedure described in WO9412505. To a solution of 3-chlorothiophene (7.00 g, 59.0 mmol) in 60 mL anhydrous THF under nitrogen was added n-butyllithium, 2.5 M in hexanes (23.6 ml, 59.0 mmol) dropwise from a plastic syringe over 15 min. The reaction became cloudy with a white ppt. The reaction was allowed to stir for 40 min, at which point trimethylsilyl chloride (8.24 ml, 64.9 mmol) was added dropwise via syringe over 5 min. The mixture was allowed to stir for 10 min, and was then warmed to 0° C. for 10 min, and 7 mL water and 35 mL brine were added. The mixture was diluted with EtOAc, and the layers separated. The aqueous layer was extracted once with EtOAc. The combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give (3-chlorothiophen-2-yl)trimethylsilane as a yellow oil.

1. customThe title compound was prepared
2. additionwas added dropwise via syringe over 5 min
3. customthe layers separated
4. extractionThe aqueous layer was extracted once with EtOAc
5. dry with materialThe combined organics were dried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-75f5b79f0a57466e859671cb4081b775

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08022221B2