Acetonitrile → Fenvalerate

HRID 1447100Notes

Reaction equation

HRID 1447100 reaction equation
[C-]#N.[K+].[C:4](#[N:6])C.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH:33]([CH3:35])[CH3:34])[C:15]([O:17][CH:18](Cl)[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:20]=2)=[O:16])=[CH:10][CH:9]=1>CCOCC>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH:33]([CH3:35])[CH3:34])[C:15]([O:17][CH:18]([C:4]#[N:6])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:20]=2)=[O:16])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 9032Potassium CyanideHCID 13061774alpha-Chloro-3-phenoxybenzyl 2-(p-chlorophenyl)-2-isopropyl-acetate

Product 1

HCID 3347Fenvalerate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.5 g of potassium cyanide were added to a mixture of 80 ml of acetonitrile and the solution obtained in Example 9 and the mixture was stirred at 20° C. for 72 hours. Ether was added to the mixture which was then filtered to remove insolubles. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 95-5 cyclohexane-acetone mixture yielded 6.5 g of RS α-cyano-3-phenoxy-benzyl 2-(p-chlorophenyl)-2-isopropyl-acetate.

Workup

  1. filtrationwas then filtered
  2. customto remove insolubles
  3. customThe filtrate was evaporated to dryness under reduced pressure
  4. customthe residue was chromatographed over silica gel
  5. washElution with a 95-5 cyclohexane-acetone mixture

Sources & evidence

ORD record
ord-2f31b6f1604d4bb3b6bbee3da4b9d7e5
Source dataset
uspto-grants-1982_02
Patent number
US04315868

Reaction notes

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