Sodium hydride → 1alpha,3beta-bis(tert-butyldimethylsilyloxy)-20-{4-ethyl-4-triethylsilyloxy-(2E)-hexenyloxy}-20-methylpregna-5,7,16-triene

Participants

Reaction Steps

1α,3β-Bis(tert-butyldimethylsilyloxy)-20-hydroxy-20-methylpregna-5,7,16-triene (400 mg, 0.698 mmol), 1-bromo-4-ethyl-4-triethylsilyloxy-(2E)-hexene (0.897 g, 2.79 mmol), sodium hydride (60% in oil, 0.168 g, 4.188 mmol), 15-crown-5 (0.14 ml, 0.698 mmol) and tetrahydrofuran (12 ml) were subjected to reaction using a procedure similar to that of Example 5(1) (3 hours), worked up and purified by column chromatography (hexane:toluene=2:1) to give the titled compound (0.35 g, 62%) as a yellow foam.

Provenance & Evidence