HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → Flucythrinate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Methyl Chloride | HCID 6327 | — |
| Reactant | Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)- | HCID 93218 | — |
| Reactant | 2-(4-Difluoromethoxyphenyl)-3-methylbutyryl chloride | HCID 13118567 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Flucythrinate | HCID 50980 | 24.8% |
Reaction Steps
A solution of α-isopropyl-4-difluoromethoxyphenylacetyl chloride (4.82 g) in methylene chloride (10 ml) is added to a methyl chloride solution (10 ml) of α-cyano-m-phenoxybenzyl alcohol (4.05 g) and pyridine (1.5 ml). The mixture is stirred over the weekend and filtered. The filtrate and the washings are evaporated and the residual oil (6.29 g) is purified on a silica column using 1:1 methylenechloride-hexane as eluent. The solvent was evaporated and the residue treated with sodium borohydride and the resulting product purified on a silica gel column to give 2.01 g of product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04239777 |
| Source dataset | uspto-grants-1980_12 |
| ORD ID | ord-506cc6e541054b999a36146d653d6630 |
| Source note | uspto-grants-1980_12 |