Hexamethyldisilazane → HCID 54478909, compound

Temperature

-78 °C

To a stirred solution of 1,1,1,3,3,3-hexamethyldisilazane (1.79 g, 11.1 mmol) in THF (37 ml) was added n-butyl lithium (1.52 M solution in hexane; 7.3 ml, 11.1 mmol) dropwise at 0° C. and the mixture was stirred at 0° c. for 30 minutes, then cooled at −78° C. A solution of 1-(4-[[tert-butyl(dimethyl)silyl]oxy]-3-ethylphenyl)-1-ethanone (2.57 g, 9.23 mmol) in THF (40 ml) was added dropwise, and the mixture was stirred at −78° c. for 1 hour. 1-(Trifluoroacetyl)imidazole (2.0 g, 12.2 mmol) was added, and the mixture was stirred at −78° c. for 3 hours, and quenched with water. The reaction mixture was warmed up to room temperature, and diluted with ethyl acetate. The whole was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was used for next reaction without further purification. (3.45 g, 99% yield).

1. stirringthe mixture was stirred at −78° c
2. waitfor 1 hour
3. stirringthe mixture was stirred at −78° c
4. waitfor 3 hours
5. customquenched with water
6. temperatureThe reaction mixture was warmed up to room temperature
7. additiondiluted with ethyl acetate
8. extractionThe whole was extracted with ethyl acetate
9. washThe organic layer was washed with brine
10. dry with materialdried over MgSO4
11. concentrationconcentrated in vacuo
12. customThe residue was used for next reaction without further purification

ORD record

ord-a86e60ac1944470289ee450660f2de51

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06727238B2