Triphenylphosphine → (S)-3,5-di-(tert-butyldimethylsilyloxy)-pentan-2-one

Participants

Reaction Steps

Ozone in O2 is directed at -78° C. through a solution of 1.610 g (4.67 mmol) of 11 in 200 ml of absolute dichloromethane (dry ice/acetone-cold bath). When starting compound 11 can no longer be detected by thin-layer chromatography in the solution, 3.89 g (14.83 mmol) of triphenylphosphine is added, and the cold bath is removed. The reaction batch is allowed to come slowly to room temperature, and the solvent is distilled off in a vacuum. Flash chromatography of the residue by a silica gel column with pentane/Et2O (50:1) yields 1.135 g (3.27 mmol, 70%) of 12.

Provenance & Evidence