HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl iodide → Methyl 1-methoxycyclopropanecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Methyl 1-hydroxy-1-cyclopropane carboxylate | HCID 2733178 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 1-methoxycyclopropanecarboxylate | HCID 20393514 | 54.8% |
Reaction Steps
According to WO 2005/014577 methyl 1-hydroxycyclopropanecarboxylate (1.01 g, 8.70 mmol) was dissolved under argon in THF (10 ml) and cooled using an ice-bath. Sodium hydride (60%, 0.52 g, 13.00 mmol) was added portionwise followed by iodomethane (1 ml, 16.06 mmol) and the mixture was stirred for 18 hours at room temperature. The mixture was quenched with saturated solution of NH4Cl (20 ml) and extracted with EtOAc. The organic extracts were combined, dried, filtered and evaporated in vacuo to give 620 mg of the crude product which was used as such.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08163724B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-b3bcf9abd66d4b6eae9b544b7fef80d4 |
| Source note | uspto-grants-2012_04 |