Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | 2,3,3-trimethyl-3H-indol-5-yl-acetic acid | HCID 14117637 | — |
| Solvent | Sulfolane | HCID 31347 | — |
| Product | HCID 67529218 | HCID 67529218 | 79% |
Reaction Steps
Methyl iodide (3 ml, 48.19 mmol) was added to a solution of 2,3,3-trimethyl-3H-indol-5-yl-acetic acid (2.5 g, 11.52 mmol) in sulfolan (15 ml). The reaction was heated at 48° C. for 18 hours, then cooled to room temperature. The crude reaction mixture was added dropwise to an excess of diethyl ether and the precipitate was collected by filtration and dried in vacuo to obtain the product as a beige solid (3.27 g, 79% yield). 1H NMR (d6-DMSO): δH 7.85 (d, 1H), 7.70 (s, 1H), 7.50 (d, 1H), 3.95 (s, 3H), 3.75 (s, 2H), 2.75 (s, 3H), 1.50 (s, 6H). MALDI-TOF, m/z 232 (M+=232 for C14H18NO2).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07662973B2 |
|---|
| Source dataset | uspto-grants-2010_02 |
|---|
| ORD ID | ord-d03fd6d80c834c9faaa7046db80bad81 |
|---|
| Source note | uspto-grants-2010_02 |
|---|