Dicyclohexylcarbodiimide → alpha-Cyano-4-fluoro-3-phenoxybenzyl 3-(n-pentyloxy)-2,2-dimethylcyclopropanecarboxylate

HRID 28102Notes

Reaction equation

HRID 28102 reaction equation
[C:1]([CH:3]([OH:18])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=1)#[N:2].[CH2:19]([O:24][CH:25]1[CH:27]([C:28](O)=[O:29])[C:26]1([CH3:32])[CH3:31])[CH2:20][CH2:21][CH2:22][CH3:23].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl.CN(C=O)C>[CH2:19]([O:24][CH:25]1[CH:27]([C:28]([O:18][CH:3]([C:1]#[N:2])[C:4]2[CH:9]=[CH:8][C:7]([F:10])=[C:6]([O:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:5]=2)=[O:29])[C:26]1([CH3:31])[CH3:32])[CH2:20][CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 103771092-(4-Fluoro-3-phenoxyphenyl)-2-hydroxyacetonitrileHCID 155857682,2-Dimethyl-3-(pentyloxy)cyclopropane-1-carboxylic acid

Product 1

HCID 23338844alpha-Cyano-4-fluoro-3-phenoxybenzyl 3-(n-pentyloxy)-2,2-dimethylcyclopropanecarboxylate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of α-cyano-4-fluoro-3-phenoxybenzyl alcohol (437 mg., 1.8 mmol), 3-(n-pentyloxy)-2,2-dimethylcyclopropanecarboxylic acid (2.0 mmol) and 4-dimethylaminopyridine (0.65 mmol) in 20 ml of methylene chloride and 2 ml of DMF is added N,N'-dicyclohexylcarbodiimide (2 mmol). The reaction mixture is stirred, under nitrogen, for about two hours and then filtered and extracted with water. The aqueous phase is extracted with ether. The combined organic phases are washed with saturated aqueons sodium bocarbonate, water and saturated aqueous sodium chloride, dried over calcium sulfate and solvent evaporated. The crude product is chromatographed on a rotary chromatograph eluting with ether/hexane to yield α-cyano-4-fluoro-3-phenoxybenzyl 3-(n-pentyloxy)-2,2-dimethylcyclopropanecarboxylate.

Workup

  1. filtrationfiltered
  2. extractionextracted with water
  3. extractionThe aqueous phase is extracted with ether
  4. washThe combined organic phases are washed with saturated aqueons sodium
  5. dry with materialwater and saturated aqueous sodium chloride, dried over calcium sulfate and solvent
  6. customevaporated
  7. customThe crude product is chromatographed on a rotary chromatograph
  8. washeluting with ether/hexane

Sources & evidence

ORD record
ord-ab86b219cf7744558d41c385c9722afd
Source dataset
uspto-grants-1980_09
Patent number
US04225533

Reaction notes

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