Water → HCID 86739863, compound

HRID 2412337Notes

Reaction equation

HRID 2412337 reaction equation
[Cl:1]/[C:2](/[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[CH:3]\[C@H:4]1[C@H:6]([C:7](Cl)=[O:8])[C:5]1([CH3:11])[CH3:10].[C-:19]#[N:20].[Na+].O.[CH:23]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:26]=1)=[O:24]>CCCCCC.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Cl:1]/[C:2](/[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[CH:3]\[C@H:4]1[C@H:6]([C:7]([O:24][CH:23]([C:19]#[N:20])[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:26]=2)=[O:8])[C:5]1([CH3:11])[CH3:10]

Participants

8

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 129410066-Phenoxypyridine-2-carbaldehydeHCID 44152741rel-(1R,3R)-3-[(1Z)-2-Chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropanecarbonyl chloride

Product 1

HCID 86739863HCID 86739863, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 8058HexaneSolvent2×

Procedure

6.7 g (0.02 mol) of (±)-trans-Z-3-(2-chloro-2-(4-chloro-phenyl)-vinyl)-2,2-dimethyl-1-cyclopropanecarboxylic acid-chloride, dissolved in 10 ml of n-hexane, were added dropwise to a mixture of 40 ml of n-hexane, 1.5 g of sodium cyanide, 2 ml of water, 3.98 g (0.02 mol) of 2-formyl-6-phenoxy-pyridine and 0.5 g of tetrabutylammonium bromide at 20° to 25° C., while stirring, and the mixture was then stirred for 4 hours at 20° to 25° C. 100 ml of toluene were then added to the reaction mixture, and the latter was extracted by shaking twice with 60 ml of water. The organic phase was separated off and dried over magnesium sulphate, and the solvent was distilled off in a water jet vacuum. The last solvent residues were removed by incipient distillation for a short time at a bath temperature of 60° C./1 mm Hg. 6.4 g (77 % of theory) of cyano-(6-phenoxy-2-pyridinyl)-methyl (±)-trans-Z-3-(2-chloro-2-(4-chloro-phenyl)-vinyl)-2,2-dimethyl-cyclopropanecarboxylate were obtained as a viscous yellow oil. The structure was established by the 1H-NMR spectrum.

Workup

  1. stirringthe mixture was then stirred for 4 hours at 20° to 25° C
  2. extractionthe latter was extracted
  3. stirringby shaking twice with 60 ml of water
  4. customThe organic phase was separated off
  5. dry with materialdried over magnesium sulphate
  6. distillationthe solvent was distilled off in a water jet vacuum
  7. customThe last solvent residues were removed by incipient distillation for a short time at a bath temperature of 60° C./1 mm Hg

Sources & evidence

ORD record
ord-4533f43dca4a4749b24540cfbee84d36
Source dataset
uspto-grants-1985_01
Patent number
US04491585

Reaction notes

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