4-Nitrobenzenesulfonyl chloride → 3-{[tert-Butyl(dimethyl)silyl]oxy}propyl 4-nitrobenzene-1-sulfonate

Participants

Reaction Steps

A solution of 3-t-butlydimethylsiloxy-1-propanol, prepared by the method of McDougal, et al. JOC, 1986, 51, 3388, which is incorporated herein by reference, (7.6 g, 40 mmol) and diisopropylethylamine (10.4 mL, 60 mmol) in methylene chloride (200 mL) at 0° C. was treated with p-nitrophenylsulfonyl chloride (9.7 g, 44 mmol), stirred for 3 h, poured into saturated NaHCO3 and extracted with diethyl ether. The extracts were washed with brine, dried (Na2SO4), and concentrated. The residue was chromatographed on silica gel with 5% ethyl acetate/hexanes to provide 6.00 g of the title compound.

Provenance & Evidence