Benzaldehyde → N-Trimethylsilylbenzaldimine

In 75 mL of anhydrous THF were added 17.29 mL (75 mmol) of hexamethyldisilazane and 30 mL (75 mmol) of N-butyllithium (2.5M in hexane) at 0° C. under nitrogen. After stirring for one hour, 7.65 mL (75 mmol) of benzaldehyde was added at room temperature, and the mixture was refluxed for 3 hours. Then, 9.52 mL (75 mmol) of freshly distilled trimethylsilyl chloride was added with a syringe. The mixture was refluxed for 2 hours. A white precipitate formed during this process. The reaction mixture was then cooled to room temperature and the liquid layer was transferred with a syringe to a distillation flask under nitrogen. The solvent was evaporated in vacuo, and the oily residue was distilled under reduced pressure (68° C./1 mm Hg) to give pure N-trimethylsilylbenzaldimine as a pale yellow oil (10.6 g, 80 %) having the identification data shown below:

1. temperaturethe mixture was refluxed for 3 hours
2. temperatureThe mixture was refluxed for 2 hours
3. customA white precipitate formed during this process
4. customthe liquid layer was transferred with a syringe to a distillation flask under nitrogen
5. customThe solvent was evaporated in vacuo
6. distillationthe oily residue was distilled under reduced pressure (68° C./1 mm Hg)

ORD record

ord-775f927e5399400bab399e533bd7fdfd

Source dataset

uspto-grants-1998_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05705508