Dicyclohexylcarbodiimide → HCID 178444551、化合物

HRID 1731461ノート

反応式

HRID 1731461 の反応式
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([OH:14])=[O:13])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH:4]=[CH2:5].[CH2:15]([O:17][C:18]1[CH:23]=[CH:22][C:21](O)=[CH:20][CH:19]=1)[CH3:16].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl.C(OCC)C>[CH2:15]([O:17][C:18]1[CH:23]=[CH:22][C:21]([O:13][C:12]([C@H:9]2[CH2:8][CH2:7][C@H:6]([CH2:1][CH2:2][CH2:3][CH:4]=[CH2:5])[CH2:11][CH2:10]2)=[O:14])=[CH:20][CH:19]=1)[CH3:16]

参加物

7

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 121504-EthoxyphenolHCID 178444555HCID 178444555、化合物

生成物 1

HCID 178444551HCID 178444551、化合物収率 83.5%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 520 mg of trans-4-(4-pentenyl)cyclohexanecarboxylic acid, 439.4 mg of p-ethoxyphenol, 765.5 mg of dicyclohexylcarbodiimide and 45 mg of 4-(dimethylamino)pyridine were dissolved in 80 ml of methylene chloride and the solution was stirred at room temperature for 20 hours. Subsequently, the reaction mixture was diluted with diethyl ether, the precipitated urea was filtered off and the filtrate was concentrated. The residue was taken up in hexane and the solution was washed with dilute hydrochloric acid, sodium hydrogen carbonate solution and water. The aqueous phases were back-extracted twice with hexane. The organic phases were dried over magnesium sulphate and evaporated. Low-pressure chromatography of the resulting residue on silica gel with ethyl acetate/petroleum ether (vol. 3:97) gave 0.7 g (83%) of trans-4-(4-pentenyl)cyclohexanecarboxylic acid p-ethoxyphenyl ester. After recrystallization from 3 ml of methanol there were finally obtained 455 mg of product in the form of colourless crystals; m.p. (C--N) 32.7° C., cl.p. (N--I) 57.5° C.

後処理

  1. filtrationthe precipitated urea was filtered off
  2. concentrationthe filtrate was concentrated
  3. washthe solution was washed with dilute hydrochloric acid, sodium hydrogen carbonate solution and water
  4. extractionThe aqueous phases were back-extracted twice with hexane
  5. dry with materialThe organic phases were dried over magnesium sulphate
  6. customevaporated

出典と根拠

ORDレコード
ord-2d184766db1f47dd88de15a2bb7df846
出典データセット
uspto-grants-1986_11
特許番号
US04621901

反応ノート

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