Imidazole → 3-O-(tert-Butyldimethylsilyl) Estrone

Participants

Reaction Steps

To a solution of 3-hydroxy-estra-1,3,5(10)-triene-17-one (100 g, 0.370 mole) in 500 ml of dichloromethane was added tert-butyldimethylsilyl-chloride (58.3 g, 0.388 mole) and imidazole (26.4 g, 0.388 mole). The mixture was stirred for 24 hours at room temperature. Water (300 ml) was added and the organic layer was washed with 200 ml of water. After concentration the product was crystallized from a mixture of ethanol/diisopropyl ether, collected by filtration and dried. It weighed 145 g (95% yield).

Provenance & Evidence