4-Bromo-N,N-dimethylbenzenesulphonamide → 4-(3-(tert-butyldimethylsilyloxy)-alpha-hydroxybenzyl)-N,N-dimethylbenzenesulfonamide

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Reaction Steps

The sulfonamide (97.45 g, 0.37 mol) was subsequently treated with n-butyllithium and 3-(tert-butyldimethylsilyloxy)benzaldehyde as described in Example 54, and the product was purified by chromatography on silica gel with hexane:ethyl acetate to give 89.5 g (57%) of 4-(3-(tert-butyldimethyl-silyloxy)-α-hydroxybenzyl)-N,N-dimethylbenzenesulfonamide as a yellow oil which crystallized on standing. A portion was recrystallized from ethanol:water to give white crystals, mp 100°-103° C. NMR (CDCl3, 60 MHz): δ0.1 (s, 6H); 0.9 (s, 9H); 2.6 (s, 6H); 3.5 (br s, 1H); 5.7 (s, 1H); 6.5-7.7 (m, 8H).

Provenance & Evidence