Ammonium Chloride → HCID 25232594, compound

Temperature

-20 °C

To a mixture of N,N,N′-trimethylethylenediamine (2.86 g) and THF (80 mL) there were added dropwise a 2.6 M hexane solution of n-butyllithium (8.46 mL), and 2-triisopropylsilanyloxazole-5-carboaldehyde [CAS No. 869542-45-0] (5.08 g), in that order at −20° C. under a nitrogen atmosphere. After stirring the mixture at −20° C. for 3 hours, the 2.6 M hexane solution of n-butyllithium (8.46 mL) was again added dropwise, stirring was continued at −20° C. for 3 hours, and then the mixture was cooled to −75° C. and 1,2-dibromotetrafluoroethane (7.12 mL) was added. The mixture was returned to room temperature, and then ethyl acetate (300 mL) and an aqueous ammonium chloride solution (300 mL) were added. After sufficiently shaking the mixture, the organic layer was separated off and dried over anhydrous magnesium sulfate. The mixture was filtered to obtain a filtrate, and the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture) to obtain the target compound (1.94 g) as a brown liquid.

1. customat −20° C.
2. stirringstirring
3. waitwas continued at −20° C. for 3 hours
4. temperaturethe mixture was cooled to −75° C.
5. customwas returned to room temperature
6. stirringAfter sufficiently shaking the mixture
7. customthe organic layer was separated off
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationThe mixture was filtered
10. customto obtain a filtrate
11. distillationthe solvent in the filtrate was distilled off under reduced pressure
12. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture)

ORD record

ord-76056c8786cb4adbaba89d7724001c14

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07807690B2