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

HRID 28102Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 28102
[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]

Komponenten

7

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ab86b219cf7744558d41c385c9722afd
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04225533

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