The Oxidation of Primary Trimethylsilyl Ethers to Aldehydes – a selective conversion of a primary hydroxy group into an aldehyde group in the presence of a secondary hydroxy group

Secondary trimethylsilyl ethers (2a–d) are not affected by Collins reagent in dichloromethane at 0°C. Primary trimethylsilyl ethers (4a–e), however, are smoothly oxidized to aldehydes (5a–e) under these conditions. In agreement with these observations trimethylsilylated diols or polyols with primary and secondary trimethylsilyloxy groups (6–9) are oxidized selectively by Collins reagent to trimethylsilyloxy aldehydes (10–13).