Methanol → HCID 70281582, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred, cooled (-45° C. bath, MeCN--CO2) solution of 21-methyl-11β-(trimethylsiloxy)-pregna-1,4,16-trien-3,20-dione (0.395 g, 0.96 mmol) in 9.0 mL of anhydrous THF under Ar was added via syringe chlorotrimethylsilane (0.50 mL, 4.0 mmol), followed by dropwise addition over 3 min of 5.0 mL (1.0 mmol) of the above cuprate solution. After 10 min, the mixture was quenched at -45° C. (bath) by rapid addition via syringe of a solution of 0.5 mL (12 mmol) of MeOH and 1.5 mL (11 mmol) of Et3N and warming to 0° C. Water and EtOAc were added and the solution was stirred vigorously. The pH was adjusted from 9 to 7 with sat. KH2PO4 and stirring was continued for 0.5 h. The layers were separated and the organic solution was washed with water and brine, dried (MgSO4), filtered and concentrated. The residue was purified by chromatography to give 0.41 g (85.5%) of the desired product, C29H48O3Si2, as a white solid.

Provenance & Evidence