Imidazole → 1-t-BUTYLDIMETHYLSILYLOXY-2,3-DIMERCAPTOPROPANE

Temperature

0 °C

To a solution of 2,3-dimercapto-1-propanol (15.0 ml, 150 mmol) and imidazole (15.3 g, 224 mmol, 1.5 eq) in THF (300 mL) was added t-butyldimethylsilyl chloride (21.4 g, 142 mmol, 0.95 eq) at 0° C. The mixture was stirred at 0° C. for 1 hr and at room temperature for 18 hr. A saturated solution of ammonium chloride was added and the aqueous phase was extracted with dichloromethane. The organic layer was dried with anhydrous sodium sulphate and the solvent was evaporated under reduced pressure. The crude material was purified by flash chromatography with a mixture of hexane and ethyl acetate (90:10) to give the pure compound (32.04 g) in 94.5% yield.

1. extractionthe aqueous phase was extracted with dichloromethane
2. dry with materialThe organic layer was dried with anhydrous sodium sulphate
3. customthe solvent was evaporated under reduced pressure
4. customThe crude material was purified by flash chromatography with a mixture of hexane and ethyl acetate (90:10)

ORD record

ord-4c630c3fba9043b79c5c1a3b2632f55d

Source dataset

uspto-grants-1999_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05955610