Aluminium lithium hydride → 4-(Tert-butyldimethylsilyloxy)-benzenemethanethiol

Participants

Reaction Conditions

Reaction Steps

to a stirred solution of ethanethioic acid, S-[4-(tert-butyldimethylsilyloxy)benzyl] ester (30.7 g, 104 mmol) in dry THF (300 mL) at 0° C. under an argon atmosphere was added lithium aluminium hydride (5.9 g, 156 mmol). The reaction was stirred for 3 h at 0° C. The mixture was quenched by careful addition of EtOAc then water. The pH was brought to 5 with an aqueous solution of 10% HCl and the resulting slurry was filtered. The filtrate was extracted with EtOAc (2×100 mL) and the combined organic layers were washed successively with Rochelle's salt, brine, dried (MgSO4), filtered and concentrated to give the product as a green oil (22.1 g, 84%).

Provenance & Evidence