Pyridine → Flucythrinate

HRID 1732901Notes

Reaction equation

HRID 1732901 reaction equation
[CH:1]([CH:4]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:15]([F:17])[F:16])=[CH:10][CH:9]=1)[C:5](Cl)=[O:6])([CH3:3])[CH3:2].CCl.[C:20]([CH:22]([OH:36])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:24]=1)#[N:21].N1C=CC=CC=1>C(Cl)Cl>[CH:1]([CH:4]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:15]([F:17])[F:16])=[CH:10][CH:9]=1)[C:5]([O:36][CH:22]([C:20]#[N:21])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:24]=1)=[O:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6327Methyl ChlorideHCID 93218Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-HCID 131185672-(4-Difluoromethoxyphenyl)-3-methylbutyryl chloride

Product 1

HCID 50980FlucythrinateYield 24.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. filtrationfiltered
  2. customThe filtrate and the washings are evaporated
  3. customthe residual oil (6.29 g) is purified on a silica column
  4. customThe solvent was evaporated
  5. additionthe residue treated with sodium borohydride
  6. customthe resulting product purified on a silica gel column

Sources & evidence

ORD record
ord-506cc6e541054b999a36146d653d6630
Source dataset
uspto-grants-1980_12
Patent number
US04239777

Reaction notes

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