Zinc powder (9.92 g, 152 mmol) and copper(I) chloride (1.50 g, 15.2 mmol) were added to 15 mL of dry benzene under nitrogen protection, stirred and refluxed for 30 min. Subsequently, trimethylchlorosilane (12.8 mL, 101 mmol) and ethyl bromoacetate (12.3 mL, 111 mmol) dissolved in a mixture of 23 mL of anhydrous tetrahydrofuran and 21 mL of anhydrous benzene were slowly added through a dropping funnel, maintaining a mild reflux condition. The titration process took about 1 hour. After dropwise addition, reflux was continued for 1 hour, followed by cooling in an ice bath. Under stirring, 30 mL of 5% aqueous hydrochloric acid solution was added through a dropping funnel in 10 minutes. The liquid layer was separated and the reaction flask was washed with ether. The organic phase was combined and washed sequentially with saturated sodium bicarbonate solution twice, saturated sodium chloride solution twice, then saturated sodium bicarbonate solution twice, and finally saturated sodium chloride solution twice. The combined organic layers were dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product. Purification by reduced pressure distillation (boiling point 93-94 °C, 104 mmHg) gave ethyl 2-(trimethylsilyl)acetate as a pale yellow liquid in 74% yield (12.0 g, 74.9 mmol).1H NMR (CDCl3) δ 4.09 (q, J = 7.1 Hz, 2H), 1.89 (s, 2H), 1.24 (t, J = 7.1 Hz. 3H), 0.12 (s, 9H).
