tert-Butyldimethylsilyl chloride → Benzenemethanol, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-

Participants

Reaction Steps

(Formula II, R1=tert-butyldimethylsilyloxymethylphenyl, R2=4-tert-butyldimethylsilyloxymethylbenzyl). Methyl 4-(hydroxymethyl)benzoate was treated with tert-butyldimethylsilyl chloride using the general procedure described in Journal of the American Chemical Society, 1972, 94, 6190. The resulting product was reduced with lithium aluminium hydride to afford 4-(tert-butyldimethylsilyloxymethyl)benzyl alcohol. This alcohol was converted into the required compound using Method C. 1H NMR (CCl4) δ 0.08 (32H, s), 0391 (18H, s), 4.22 (1H, d, J 2 Hz), 4.68 (5H, br s), 4.90 (2H, a), 7.1-7.6 (8H, m); MS (CH4) 483 (M+−CH3, 52%), 133 100%).

Provenance & Evidence