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

Temperature

10 °C

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).

1. temperatureAfter the completion of the Grignard formation, the reaction mixture was cooled to 0° C.
2. stirringthe reaction mixture was stirred overnight at room temperature
3. customThe reaction mixture was quenched with water (20 mL) at 0° C.
4. extractionthe organics were extracted with t-butyl methyl ether (2×20 mL)
5. customThe combined organic layers were dried
6. concentrationconcentrated under reduced pressure
7. customto obtain the crude product

ORD record

ord-8a2b67484fa7406398a259105b07dad1

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687496B2