Moisture SensitiveFlammables area
Alvisi, C. et al.: J. Org. Chem., 63, 1330 (1998): Higashiya, S. et al.: J. Org. Chem., 69, 6326 (2004); Hicks, J.D. et al.: Org. Lett., 9, 5621 (2007);
Silylation of alcohols in the presence of e.g. pyridine: J. Chem. Soc., Chem. Commun., 156 (1979); imidazole-DMF: Helv. Chim. Acta, 64, 2002 (1981); or catalyzed by DMAP: J. Org. Chem., 52, 598 (1987) have been reported. The TES group is readily cleaved with TBAF or other F- reagents. Catalytic amounts of FeCl3 in MeOH has also been recommended: Synlett, 1260 (2006). Selective cleavage in the presence of TBDMS has been achieved with aqueous AcOH in THF: Liebigs Ann. Chem., 1281 (1986), or 2% HF in acetonirile: Tetrahedron Lett., 26, 5239 (1985).
Silylation reagent (see Appendix 4). Generally, triethylsilyl (TES) ethers are 10-100x more stable to hydrolysis than their TMS (see Chlorotrimethylsilane, A13651) counterparts but much less so than TBDMS (see tert-Butyldimethylchlorosilane, A13064): J. Org. Chem., 48, 1970 (1983).