Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 2,4,6-Trichlorobenzoyl chloride | HCID 2733703 | — |
| Reactant | Potassium bis(trimethylsilyl)amide | HCID 3251421 | — |
| Reactant | HCID 15292264 | HCID 15292264 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Hexamethylphosphoramide | HCID 12679 | — |
| Product | HCID 15292265 | HCID 15292265 | — |
Reaction Steps
To 5-methoxy-2-methyl-3-indolyl acetic acid 2-(trimethylsilyl)ethyl ester (2.00 g) in THF (20.0 mL) was added HMPA (2.0 mL). To the resulting mixture at -78° C. was added a 0.5M toluene solution of KHMDS (13.8 mL). After a period of 0.5 h, 2,4,6-trichlorobenzoyl chloride (1.03 mL) was added and the mixture was stirred 0.5 h at -78° C. then 0.5 h at 0° C. An aqueous solution of NH4Cl was then added and extracted with EtOAc. After purification by flash chromatography (10% EtOAc in hexane) the title compound was obtained (2.80 g) and used as such for the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05436265 |
|---|
| Source dataset | uspto-grants-1995_07 |
|---|
| ORD ID | ord-91ade6e8e69b45a5b50a15a0ae4e91e1 |
|---|
| Source note | uspto-grants-1995_07 |
|---|