(1-Oxo-2-propenyl)trimethylsilane(CAS no.: 51023-60-0), which is also known as Silane, trimethyl(1-oxo-2-propenyl)-, could be produced through the following synthetic routes.

A. (1-Hydroxy-2-propenyl)trimethylsilane. A 2-L, three-necked, round-bottomed flask is equipped with a magnetic stirring bar, two pressure-equalizing dropping funnels (250 and 500 mL), and a Claisen adapter fitted with an argon inlet adapter and a rubber septum. The flask is charged with 20.0 g (0.344 mol) of allyl alcohol, and 400 mL of dry tetrahydrofuran, and then cooled below -75°C with a dry ice–acetone bath and maintained at that temperature while 157 mL (0.363 mol) of a 2.31 M solution of n-butyllithium in hexane is added dropwise over 1 hr. After 50 min, a solution of 39.3 g (0.362 mol) of chlorotrimethylsilane in 25 mL of tetrahydrofuran is added dropwise via syringe over 30 min, and the resulting colorless reaction mixture is stirred for 1 hr further, and then treated dropwise over 1.5 hr with 258 mL (0.415 mol) of a 1.61 M solution of tert-butyllithium in pentane. After 2 hr of further stirring at -75°C the cold bath is removed, and 100 mL of saturated ammonium chloride solution is added in one portion to the yellow reaction mixture. The resulting solution is stirred for 5 min and then diluted with 50 mL of water and 300 mL of pentane. The organic phase is separated and washed successively with three 100-mL portions of water and two 100-mL portions of saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated by carefully distilling off the solvents at atmospheric pressure through a 10-cm Vigreux column. The residual pale yellow liquid is transferred to a 100-mL round-bottomed flask, and the remaining volatile impurities are removed by distillation at 15 mm through a 4-cm column packed with glass helices, leaving 35.1–39.7 g of (1-hydroxy-2-propenyl)trimethylsilane as a pale-yellow liquid used in the next step without further purification.

B. (1-Oxo-2-propenyl)trimethylsilane. A 2-L, three-necked, round-bottomed flask is equipped with a mechanical stirrer and two 250-mL pressure-equalizing dropping funnels, one of which is fitted with an argon inlet adapter. The flask is charged with 41.71 g (0.329 mol) of oxalyl chloride and 500 mL of dichloromethane, and cooled below -75°C with a dry ice–acetone bath and maintained at that temperature while a solution of 55.82 g (0.715 mol) of dimethyl sulfoxide in 60 mL of dichloromethane is added dropwise over 1 hr. After 1 hr, a solution of the crude (1-hydroxy-2-propenyl)trimethylsilane in 100 mL of dichloromethane is added dropwise over 1.25 hr to the colorless reaction mixture, which is stirred at -75°C for 1 hr further, and then treated dropwise over 30 min with 150.38 g (1.486 mol) of triethylamine. After 1 hr, the cold bath is removed and the reaction mixture is poured into 200 mL of water. The organic phase is separated and washed successively with five 100-mL portions of 10% hydrochloric acid, three 100-mL portions of water, and two 100-mL portions of saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated by carefully distilling off the solvents at atmospheric pressure through a 10-cm Vigreux column. The residual yellow oil is transferred to a 250-mL, round-bottomed flask containing 0.050 g of 3-tert-butyl-4-hydroxy-5-methylphenyl sulfide and distilled through a 4-cm column packed with glass helices to afford 27.8–30.0 g (63–68% overall yield based on allyl alcohol) of (1-oxo-2-propenyl)trimethylsilane as a brilliant-yellow oil, bp 47–50°C (30 mm).