Ethyl cyanoformate → Ethyl 6-chloro-5-methoxy-1-oxoindane-2-carboxylate

Temperature

-78 °C

To a solution of 6-chloro-5-methoxyindan-1-one (27.6 g, 141 mmol) in THF (630 mL) at −78° C. was added a 1.0M solution of lithium bis(trimethylsilyl)amide in THF (309 mL, 309 mmol) and then the solution was slowly warmed to ca −50° C. during 1 hour. After re-cooling to −78° C., ethyl cyanoformate (21.3 mL, 216 mmol) was introduced and the reaction mixture was allowed to warm to room temperature during 2 hours. After quenching with 300 mL of 1N HCl, most of the THF was removed by rotary evaporation under reduced pressure. The residual mixture was extracted with EtOAc and the organic layer was washed with dilute aqueous NaHCO3 and dried over Na2SO4. Filtration through a pad of silica and removal of the solvent under reduced pressure gave ethyl 6-chloro-5-methoxy-1-oxoindane-2-carboxylate as a brown oil.

1. temperaturethe solution was slowly warmed to ca −50° C. during 1 hour
2. temperatureto warm to room temperature during 2 hours
3. customAfter quenching with 300 mL of 1N HCl, most of the THF
4. customwas removed by rotary evaporation under reduced pressure
5. extractionThe residual mixture was extracted with EtOAc
6. washthe organic layer was washed with dilute aqueous NaHCO3
7. dry with materialdried over Na2SO4
8. filtrationFiltration
9. customthrough a pad of silica and removal of the solvent under reduced pressure

ORD record

ord-7b7e6d8bb18c4ac1a43886ab7ef0289e

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07709508B2