Pyridine → HCID 13246114, compound

HRID 647550Notes

Reaction equation

HRID 647550 reaction equation
[Cl:1][C:2]([Cl:11])=[CH:3][CH:4]([CH:8]([CH3:10])[CH3:9])[C:5](Cl)=[O:6].[C:12]([CH:14]([OH:28])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]=1)#[N:13].N1C=CC=CC=1>C1C=CC=CC=1.C(OCC)C>[Cl:1][C:2]([Cl:11])=[CH:3][CH:4]([CH:8]([CH3:10])[CH3:9])[C:5]([O:28][CH:14]([C:12]#[N:13])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:16]=1)=[O:6]

Participants

6

Reactant 3

HCID 1049PyridineHCID 93218Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-HCID 20485210HCID 20485210, compound

Product 1

HCID 13246114HCID 13246114, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

In 20 ml of dry benzene were dissolved 2.0 g of α-(2,2-dichlorovinyl)isovaleric acid, followed by the addition of 6.0 g of thionyl chloride. The mixture was refluxed overnight. It was then distilled to remove the low-boiling fraction, whereby α-(2,2-dichlorovinyl)isovaleroyl chloride was obtained. This α-(2,2-dichlorovinyl)isovaleroyl chloride was dissolved in 25 ml of dry benzene, followed by the addition of 2.3 g of α-cyano-3-phenoxybenzyl alcohol and, then, 2.4 g of pyridine. The mixture was stirred at room temperature overnight. The resultant reaction mixture was diluted with diethyl ether, washed with water and dilute aqueous hydrogen chloride, dried over anhydrous magnesium sulfate and distilled to remove the low-boiling fraction. Column chromatography was carried out on the residue to obtain 3.2 g of α-cyano-3-phenoxybenzyl α-(2,2-dichlorovinyl)isovalerate (Compound [1]) which was shown to have the properties given below [yield: 78% based on α-(2,2-dichlorovinyl)isovaleric acid].

Workup

  1. customThe resultant reaction mixture
  2. washwashed with water and dilute aqueous hydrogen chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled
  5. customto remove the low-boiling fraction

Sources & evidence

ORD record
ord-7b59114d4d62440a92368806fcd1c012
Source dataset
uspto-grants-1983_10
Patent number
US04409238

Reaction notes

Loading…