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Trimethylsilyl Blocking Agent
Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure.
Ethyl trimethylsilylacetate; Ethyl(trimethylsilyl)acetate; (Trimethylsilyl)acetic acid ethyl ester; Acetic acid (trimethylsilyl)-, ethyl ester
Boiling Point: 157-8°
EINECS Number: 223-783-2
Molecular Weight: 160.29
Specific Gravity: 0.876
Flashpoint: 35°C (95°F)
HMIS Key: 2-3-0-X
Hydrolytic Sensitivity: 2: reacts with aqueous acid
Refractive Index: 1.4149
Application: Review of synthetic utility.1
In combination with LDA converts ketones to ?,?-unsaturated esters.2
Promotes the addition of alkylnitriles to imines.3
Reagent for conversion of carboxylic acids to ?-hydroxyesters.4
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. 297-299.
2. Larson, G. L. et al. Synth. Commun. 1999, 20, 1095.
3. Poisson, T. et al. J. Org. Chem. 2009, 74, 3516.
4. Wadhwa, K.; Verkade, J. J. Org. Chem. 2009, 74, 4368.
Fieser: F&F: Vol. 7, p 150; Vol. 11, p 234, p 237.