G. Bolton
Apr 15, 2001
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Abstract
(R = Et) [18457-03-9] C8H16O4Si (MW 204.30) InChI = 1S/C8H16O4Si/c1-5-11-7(9)6-8(10)12-13(2,3)4/h5-6H2,1-4H3 InChIKey = PVXMKQLVICGFSI-UHFFFAOYSA-N (R = Me) [51849-23-1] C7H14O4Si (MW 190.27) InChI = 1S/C7H14O4Si/c1-10-6(8)5-7(9)11-12(2,3)4/h5H2,1-4H3 InChIKey = DPVCHJXFVHLEDC-UHFFFAOYSA-N (synthesis of β-keto esters1-3) Physical Data: R = Et, bp 75 °C/0.5 mmHg, d 1.000 g cm−3; R = Me, bp 105–110 °C/19 mmHg. Preparative Methods: ethyl trimethylsilyl malonate is commercially available, or it may be easily prepared from the potassium salt of Ethyl Malonate.1, 2, 6 Methyl trimethylsilyl malonate has been prepared from t-butyl methyl malonate by treatment with Trimethylsilyl Trifluoromethanesulfonate,4 or from Meldrum's acid (2,2-Dimethyl-1,3-dioxane-4,6-dione) and methyl trimethylsilyl ether.5 The preparation and use of t-butyl trimethylsilyl malonate has been reported, although it has not been isolated and characterized.7, 8 Handling, Storage, and Precautions: the ethyl derivative is reported to be moisture sensitive.