HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → HCID 70869096, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 1H-Pyrrole-2-carboxylic acid, 5-methyl-, ethyl ester | HCID 96598 | — |
| Reactant | Cyclohexane, (bromomethyl)- | HCID 137636 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 70869096 | HCID 70869096 | 82% |
Reaction Steps
A solution of ethyl 5-methyl-1H-pyrrole-2-carboxylate (15.0 g, 98.0 mmol), (bromo-methyl)cyclohexane (17.6 g, 100 mmol) and K2CO3 (41.4 g, 300 mmol) in dry DMF (150 mL) was stirred at 50° C. overnight, then cooled to rt and filtered. To the filtrate was added NaH (12.0 g, 60%, 300 mmol) slowly. Then the mixture was stirred overnight at 50° C. The reaction mixture was quenched with water and extracted with EA twice. The combined organic phases were washed with water (3×) and brine (2×), dried over Na2SO4, filtered, concentrated and purified by CC (EA/PE=1/20) to give compound 1a (19.9 g, 82%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08946446B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-0a8e1da8068f45378b1141557e864230 |
| Source note | uspto-grants-2015_02 |