Cleavage of tert-butyldimethylsilyl ethers by chloride ion

Tetrahedron Letters

Volumn 39, Issue 3-4, 1998, Pages 327-330

  Farràs, Jaume ^a   Serra, Carme ^a   Vilarrasa, Jaume ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIDE ION; FUNCTIONAL GROUP; SILANE DERIVATIVE; TERT BUTYLDIMETHYLSILYL ETHER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DECOMPOSITION; REACTION ANALYSIS; TEMPERATURE;

EID: 0032518768     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10479-8     Document Type: Article

References (24)

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21. 12. We observed a 15-25% of cleavage when no water was added to the reaction mixture. We attribute it to the residual water present in the solvent (see Perrin, D.D; Armarego, W.F.L; Perrin, D.R. Purification of Laboratory Chemicals. Pergamon Press: Oxford, 1986, p. 224 and references therein).
22. 2O/DMSO.
23. 4, and the solvent removed. The residual amount of DMF present in the crude can be easily removed by coevaporation with toluene. Finally, the residue is chromatographed over silica gel to afford the corresponding alcohols. If the alcohol is soluble in water no extraction is performed but DMF is removed directly in a vacuum evaporator.
24. 15. In order to keep an accurate control over the amount of water which is present in the reaction we use commercially dry DMF previously stored over 4 Å molecular sieves and LiCl previously dried in a vacuum oven. We have also found useful to carry out the reaction on a sealed tube in order to avoid loss of water on heating.