Pyridine → Flucythrinate

HRID 1074898Notes

Reaction equation

HRID 1074898 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].[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>CCOCC>[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: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:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

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

Product 1

HCID 50980Flucythrinate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of α-isopropyl-4-difluoromethoxyphenylacetyl chloride (4.58 mmol) in ether (5 ml) is added to an ether (20 ml) solution of α-cyano-m-phenoxybenzyl alcohol (4.58 mmol) and pyridine (0.5 ml). The mixture is stirred overnight and filtered. The filtrate and the washings are evaporated and the residual oil is purified on 5×20 cm silica gel plates using 1:1 methylenechloride-hexane as eluent. The band in the silica gel plate is extracted with ether and evaporated to give the desired ester as an oil.

Workup

  1. filtrationfiltered
  2. customThe filtrate and the washings are evaporated
  3. customthe residual oil is purified on 5×20 cm silica gel plates
  4. extractionThe band in the silica gel plate is extracted with ether
  5. customevaporated

Sources & evidence

ORD record
ord-c4a8bf110661440296fd9f3812e1b126
Source dataset
uspto-grants-1983_07
Patent number
US04394388

Reaction notes

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