Dichloromethane → 3-((Tert-butyldimethylsilyl)oxy)propanal

Participants

Reaction Steps

To a 500 ml round bottom flask was introduced 5.23 g (27.5 mmol) of 3-t-butyldimethylsilyloxypropanol (prepared according to the method of McDougal et al, J. Org. Chem. 1986, 51, 3388), to which was added 175 ml CH2Cl2, and 8.13 g (36.4 mmol, 1.3 eq) of pyridinium chlorochromate. The reaction was stirred 90 minutes, diluted with ether, and filtered through Florisil™. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel using 10% ether in hexane. This afforded 2.63 g (50%) of the product, 3-t-butyldimethylsilyloxypropanal.

Provenance & Evidence