62515-35-9Relevant articles and documents
A New Synthesis of an Important Prostaglandin Intermediate by Selective Oxidation of a Trimethylsilylated Primary Alcohol to the Corresponding Aldehyde
Mahrwald, Rainer,Theil, Fritz,Schick, Hans,Palme, Hans-Joachim,Nowak, Heidrun,et al.
, p. 1012 - 1013 (1987)
The bis(trimethylsilyl) ether of the prostaglandin precursor rac-3 was oxidized with high selectivity to the trimethylsilylated Corey aldehyde rac-1f using Collins reagent (chromium(VI) oxide/pyridine) in dichloromethane.This unstable compound was subjected without isolation to a twophase Horner olefination by adding the dimethyl phosphonate 4 and concentrated aqueous sodium hydroxide to the oxidation mixture.Thus, the prostaglandin intermediate rac-5 was obtained in a yield of 35-40percent in a convenient one-pot procedure.