Triphenylphosphine → HCID 10845239, compound

Participants

Reaction Steps

A solution of the olefinic ester, methyl 2-(1,1-dimethylethyl)-2-methyl-4-pentenoate (2.76 g, 15 mmol), in dry CH2Cl2 (60 mL) was reacted with ozone at -78° C. When excess ozone was observed (blue coloration), nitrogen was bubbled through the solution, and Ph3P (5.90 g, 22.5 mmol) was added in one portion while stirring. The system was allowed to warm to room temperature (ca. 2 h) and stirred for 2 more hours. The solvent was removed in vacuo and the residue triturated with hexanes (150 mL). The precipitated Ph3PO (ca. 5.78g) was filtered off and the filtrate concentrated in vacuo to give 2.80 g of the crude product as a colorless viscous residue. Flash chromatography over silica gel (hexanes-EtOAc, 19:1) afforded 2.12 g (76%) of the aldehyde as a colorless oil.

Provenance & Evidence