Chlorotrimethylsilane → HCID 54410387, compound

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Reaction Steps

To a dispersion of 3.1 g of NaH in 20 mL of tetrahydrofuran (THF) at room temperature was added 20 mL of diethylmethylmalonate, at an addition rate of 0.5 mL/minute. The mixture was kept below 30° by the use of a water/ice bath. After complete addition of the diethylmethylmalonate, the mixture was stirred for 30 minutes, then cooled to 0° and 13.5 mL of chlorotrimethylsilane was added. After 40 minutes, 10 mL of hexane was added and the mixture was stirred overnight, filtered under argon, and distilled A forerun (40°-58°, 0.32 mm) was discarded, the product distilling at 62°-64°, 0.40 mm. NMR. (CD3CN, TMS) indicates that the product is a 75/25 mixture of E/Z isomers of ECPS; major isomer: 0.303 (s, 9H, SiMe3); 1.255 (t, J=b 7 Hz, 6H, OCH2CH3); 1.754 (s, 3H, vinyl CH3); 3.988-4.250 (m, all OCH2 for both isomers. Minor isomer: 0.308 (s, 9H, SiMe3); 1.264 (t, J=7H, 6H, OCH2CH3); 1.727 (s, 3H, vinyl CH3 1.754); 3.988-4.250 (m, all OCH2 for both isomers). Anal. calc. for C11H22SiO4 : C 53.67; H 8.94. Found C 53.33; H 8.76.

Provenance & Evidence