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2-(TRIMETHYLSILOXY)FURAN
Boiling Point: 40-2° / 25
Molecular Weight: 156.26
Specific Gravity: 0.950
Flashpoint: 18°C (64°F)
HMIS Key: 2-4-1-X
Hydrolytic Sensitivity: 7: reacts slowly with moisture/water
Formula: C7H12O2Si
Refractive Index: 1.436
Application: Review of synthetic utility.1
Reviewed with other similar heterocycles.2
Used in a vinylogous Mannich reaction to form aminomethyl butenolides.3
Employed in asymmetric vinylogous aldol reaction with aldehydes.4
Adds to allyl acetates to form 5-allyl-?-butenolides.5
Reference: 1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 684-693.
2. Casiraghi, G. et al. Synlett 2009, 1525.
3. Akiyama, T. et al. Adv. Synth. Catal. 2008, 350, 399.
4. Singh, R. P. et al. J. Am. Chem. Soc. 2010, 132, 9558.
5. Cho, C.-W.; Krische, M. J. Angew. Chem., Int. Ed. Engl. 2004, 43, 6689.
Additional Properties: Inhibited with BHT
Metal-Organics
Silanes