Chlorotrimethylsilane → HCID 86640243, compound

Temperature

-72.5 °C

To a stirred solution of 4-cyclohexylaniline (5 g, 28.6 mmol) in 75 ml of dry THF at −70 to −75° C. was added slowly by syringe a solution of 17.7 ml of 1.6 M n-butyllithium. When addition was complete, the resulting mixture was stirred at −70 to −75° C. for 0.5 h. To the stirred mixture was then added 3.61 ml (28.5 mmol) of chlorotrimethylsilane at −70 to −75° C. The mixture was then allowed to warm to RT and stirred at RT for 1.75 h. The mixture was then again cooled to −70 to −75° C. after which was slowly added 17.5 ml of 1.6 M n-butyllithium in hexanes. The mixture was allowed to stir at −70 to −75° C. for 0.5 h after which was added 2.45 ml (28.6 mmol) of epibromohydrin. The mixture was allowed to warm to room temperature and stirred for 2 h at room temperature. The mixture was then poured into 250 ml of cold saturated aqueous sodium bicarbonate, extracted with ethyl acetate, washed with brine, dried (sodium sulfate) and concentrated to provide an orange oil which was then purified by chromatography on silica gel, eluting with ethyl acetate/heptane to provide 3.06 g of the title compound.

1. additionWhen addition
2. temperatureto warm to RT
3. stirringstirred at RT for 1.75 h
4. temperatureThe mixture was then again cooled to −70 to −75° C. after which
5. stirringto stir at −70 to −75° C. for 0.5 h after which
6. temperatureto warm to room temperature
7. stirringstirred for 2 h at room temperature
8. extractionextracted with ethyl acetate
9. washwashed with brine
10. dry with materialdried (sodium sulfate)
11. concentrationconcentrated
12. customto provide an orange oil which
13. customwas then purified by chromatography on silica gel
14. washeluting with ethyl acetate/heptane

ORD record

ord-bb8f469534cf4a44aa9205c942a237bb

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642603B2