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

HRID 28102ノート

反応式

HRID 28102 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ab86b219cf7744558d41c385c9722afd
出典データセット
uspto-grants-1980_09
特許番号
US04225533

反応ノート

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