1,1-Dibromoethane → 3,3-Dimethoxypropyl dimethylvinylsilane

Participants

Reaction Conditions

Reaction Steps

To a stirring magnesium granules (365 mg) in anhydrous tetrahydrofuran (15 mL), few drops of dibromoethane (˜50 μL) was added at room temperature under argon and the resultant mixture was stirred for 10 min. The reaction mixture was cooled to 10° C. and 3-bromopropionaldehyde dimethyl acetal (2.2 g) was introduced dropwise during 10 min. and allowed to stir at room temperature for 2 hours. After the completion of the Grignard formation, the reaction mixture was cooled to 0° C. and chlorodimethylvinylsilane (1.2 g) was added dropwise and the reaction mixture was stirred overnight at room temperature. The reaction mixture was quenched with water (20 mL) at 0° C. and the organics were extracted with t-butyl methyl ether (2×20 mL). The combined organic layers were dried and concentrated under reduced pressure to obtain the crude product. The pure product was obtained upon vacuum distillation of the crude material at 100° C. (2 mm Hg) in 80% yield (1.5 g).

Provenance & Evidence