Dicyclohexylcarbodiimide → HCID 178444551, 화합물

HRID 247694

반응식

HRID 247694 반응식
[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]

참가 물질

7

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 121504-EthoxyphenolHCID 178444555HCID 178444555, 화합물

생성물 1

HCID 178444551HCID 178444551, 화합물수율 83.5%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

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 an 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.

후처리

  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

출처 및 근거

ORD 기록
ord-88d42fa00ec645d7b222c81884225647
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04709030

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