Sodium Chloride → ethyl (2Z)-3-{1-[(4-bromophenyl)sulfonyl]-1H-indol-2-yl}acrylate

Temperature

-70 °C

To a solution of 0.4 mL of ethyl di-o-tolylphosphonoacetate in 15 mL of THF was added 0.67 g of a 40% benzyltrimethylammonium hydroxide-methanol solution under cooling in a dry ice-acetone bath, and the resulting mixture was stirred at −70° C. for 15 minutes. To the solution, a solution of 0.47 g of 1-[(4-bromophenyl)sulfonyl]-1H-indole-2-carbaldehyde in 5 mL of THF was added, the resulting mixture was stirred at −70° C. for 1.5 hours and under cooling in an ice-methanol bath for 1 hour. To the solution, 50 mL of saturated aqueous sodium chloride solution was added, the mixture was extracted with 100 mL of ethyl acetate, the extract was washed with water and saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-hexane=1:5) to obtain 0.53 g of ethyl (2Z)-3-{1-[(4-bromophenyl)sulfonyl]-1H-indol-2-yl}acrylate as a pale yellow syrup. ESI−: 432, 434

1. temperatureunder cooling in a dry ice-acetone bath
2. stirringthe resulting mixture was stirred at −70° C. for 1.5 hours
3. temperatureunder cooling in an ice-methanol bath for 1 hour
4. extractionthe mixture was extracted with 100 mL of ethyl acetate
5. washthe extract was washed with water and saturated aqueous sodium chloride solution
6. dry with materialdried over anhydrous sodium sulfate
7. customthe solvent was evaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (ethyl acetate-hexane=1:5)

ORD record

ord-97cd595b10774946a0ddfbc9411f72dc

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07855225B2