tert-Butyldimethylsilyl chloride → HCID 54390314, compound

Participants

Reaction Steps

To a stirred solution of 10.00 g (44.1 mmol) of the product of Step A in 100 mL methylene chloride was added 6.468 g (52,9 mmol) of 4-dimethyl-aminopyridine, 7.980 g (52.9 mmol) of tert-butyldimethylchlorosilane and the mixture was stirred at room temperature for 3 hours. The reaction mixture was partitioned between methylene chloride and water, the organic layer was separated washed with 1.0N HCl, 5% NaHCO3, dried (MgSO4), filtered and evaporated. The residue was dissolved in 35 mL of anhydous THF, magnetically stirred at 0° C., and then treated with 100 mL of a 1.0M solution of lithium triethylborohydride under a nitrogen atmosphere. The reaction was allowed to warm to room temperature, and treated with several mL water until hydrogen evolution ceased. The reaction mixture was evaporated in vacuo, redissolved in methylene chloride, dried (MgSO4), filtered and reevaporated in vacuo. The residue was finally redisolved in 30 mL THF and treated with 45 mL of a 1.0M solution of tetrabutylammonium fluoride in THF while stirring for 12 hours at room temperature. The reaction mixture was then evaporated to an oil and purified on a silica gel flash chromatography column eluted with methylene chloride to afford 4.992 g (57%) of the title compound.

Provenance & Evidence