CID 6327156 → HCID 131733867, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 16D (11.2 g, 22.03 mmol) in THF (70 ml) and water (20 ml) at 0° C. was added a solution of lithium peroxide [prepared by adding hydrogen peroxide (11.25 ml, 110 mmol) to lithium hydroxide (1.387 g, 33.0 mmol) in water (20 ml)] dropwise. The mixture was stirred at 0° C. for 1 h, then quenched with sat. sodium sulfite, and organic solvent was removed under reduced pressure. The remaining solution was diluted by 50 ml of water and extracted with dichloromethane (2×20 ml). The aqueous layer was acidified using conc. HCl. The solution was then extracted with ethyl acetate (3×). The organic extracts was combined and washed with brine and dried over sodium sulfate. The solution was filtered, concentrated and dried in vacuo to give 16E (8 g, 22.91 mmol, 104% yield) as an oil. MS (ESI) (m/z): 347, 349.4 (M−H)+.

Provenance & Evidence