HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl chloroformate → Methyl 2-(Difluoromethyl)-4-(2-methylpropyl)-5-[(methoxycarbonyl)thio]-6-(trifluoromethyl)-3-pyridinecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl chloroformate | HCID 6586 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methyl 2-(difluoromethyl)-4-isobutyl-5-mercapto-6-(trifluoromethyl)-3-pyridinecarboxylate | HCID 9974711 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 2-(Difluoromethyl)-4-(2-methylpropyl)-5-[(methoxycarbonyl)thio]-6-(trifluoromethyl)-3-pyridinecarboxylate | HCID 22668810 | 77% |
Reaction Steps
To a stirred solution of 3.05 g (0.0089 mol) of product of example 1 and 0.094 g (0.01 mol) of methyl chloroformate in 25 mL dry THF was added 1.16 g (0.012 mol) of triethylamine dropwise at room temperature. After stirring for 30 min, the solvent was evaporated under reduced pressure. The residue was diluted with 100 mL of water and extracted with ether (3×50 mL). The combined organic layers were washed with water, dried (MgSO4) and evaporated. Purification of the residue by preparative HPLC (5% ethyl acetate-hexane) gave 2.75 g (77%) of product as a yellow oil: nD25 1.5830.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06605624B1 |
| Source dataset | uspto-grants-2003_08 |
| ORD ID | ord-c25c17ef8907471f8ef0d0fd14a7ab5d |
| Source note | uspto-grants-2003_08 |