HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → HCID 86720827, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-(2-Bromoethyl)-1,3-dioxolane | HCID 87776 | — |
| Reactant | ethyl 1H-pyrazole-4-carboxylate | HCID 142179 | — |
| Product | HCID 86720827 | HCID 86720827 | 59% |
Reaction Steps
To an ice-cooled stirred solution of ethyl 1H-pyrazole-4-carboxylate (2.0 g, 14.3 mmol) in DMF (10 mL) was added sodium hydride (60% dispersion in mineral oil, 0.68 g, 17.1 mmol). The reaction mixture was allowed to warm to RT over 20 minutes and 2-(2-bromoethyl)-1,3-dioxolane (2.84 g, 15.7 mmol) added. The reaction mixture was heated at 60° C. for 16 hours. The reaction was partitioned between ethyl acetate and brine. The organic phase was washed with further brine, dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure. The residue was purified by flash column chromatography eluting with 0-100% ethyl acetate in iso-hexane to afford the title compound (2.14 g, 59%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08987299B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-75fc2d24fe7845d9942496cbf34db78d |
| Source note | uspto-grants-2015_03 |