Pyridine → Flucythrinate

HRID 354735Notes

Reaction equation

HRID 354735 reaction equation
[F:1][CH:2]([F:17])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH:14]([CH3:16])[CH3:15])[C:11](Cl)=[O:12])=[CH:6][CH:5]=1.[C:18]([CH:20]([OH:34])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:22]=1)#[N:19].N1C=CC=CC=1>C(Cl)Cl>[CH:14]([CH:10]([C:7]1[CH:8]=[CH:9][C:4]([O:3][CH:2]([F:17])[F:1])=[CH:5][CH:6]=1)[C:11]([O:34][CH:20]([C:18]#[N:19])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:22]=1)=[O:12])([CH3:16])[CH3:15]

Participants

5

Reactant 3

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

Product 1

HCID 50980FlucythrinateYield 24.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(4-difluoromethoxyphenyl)-3-methylbutyryl chloride (4.82 g) in methylene chloride (10 ml) is added to a methylene chloride solution (10 ml) of α-cyano-m-phenoxybenzyl alcohol (4.05 g) and pyridine (1.5 ml). The mixture is stirred for approximately 60 hours 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 an eluant. The solvent is evaporated and the residue treated with sodium borohydride. The resulting crude material is purified on a silica gel column to yield 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 is evaporated
  5. additionthe residue treated with sodium borohydride
  6. customThe resulting crude material is purified on a silica gel column

Sources & evidence

ORD record
ord-fcde79c2ebb34747a1b966c0a742421b
Source dataset
uspto-grants-1983_03
Patent number
US04377531

Reaction notes

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