Water → [4-(4-[6-Acryloyloxyhexyloxy]-phenylcarbonyloxy)-phenyl]-methyl 2,5-bis(4-[6-acryloyloxyhexyloxy]-phenylcarbonyloxy)-benzoate

HRID 233417노트

반응식

HRID 233417 반응식
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([O:36][C:37]2[CH:45]=[CH:44][C:43]([O:46][C:47]([C:49]3[CH:54]=[CH:53][C:52]([O:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][O:62][C:63](=[O:66])[CH:64]=[CH2:65])=[CH:51][CH:50]=3)=[O:48])=[CH:42][C:38]=2[C:39]([OH:41])=[O:40])=[O:35])=[CH:30][CH:29]=1)(=[O:19])[CH:17]=[CH2:18].[C:67]([O:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][O:78][C:79]1[CH:84]=[CH:83][C:82]([C:85]([O:87][C:88]2[CH:93]=[CH:92][C:91]([CH2:94]O)=[CH:90][CH:89]=2)=[O:86])=[CH:81][CH:80]=1)(=[O:70])[CH:68]=[CH2:69].O>CN(C)C1C=CN=CC=1.ClCCl>[C:16]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]([O:36][C:37]2[CH:45]=[CH:44][C:43]([O:46][C:47]([C:49]3[CH:50]=[CH:51][C:52]([O:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][O:62][C:63](=[O:66])[CH:64]=[CH2:65])=[CH:53][CH:54]=3)=[O:48])=[CH:42][C:38]=2[C:39]([O:41][CH2:94][C:91]2[CH:92]=[CH:93][C:88]([O:87][C:85]([C:82]3[CH:83]=[CH:84][C:79]([O:78][CH2:77][CH2:76][CH2:75][CH2:74][CH2:73][CH2:72][O:71][C:67](=[O:70])[CH:68]=[CH2:69])=[CH:80][CH:81]=3)=[O:86])=[CH:89][CH:90]=2)=[O:40])=[O:35])=[CH:32][CH:33]=1)(=[O:19])[CH:17]=[CH2:18]

참가 물질

7

반응물 4

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 223924272,5-Di-[4-(6-acryloyloxyhexyloxy)benzoyloxy]benzoic acidHCID 23355771[4-(4-[6-Acryloyloxyhexyloxy]-phenylcarbonyloxy)phenyl]methanol

생성물 1

HCID 54111458[4-(4-[6-Acryloyloxyhexyloxy]-phenylcarbonyloxy)-phenyl]-methyl 2,5-bis(4-[6-acryloyloxyhexyloxy]-phenylcarbonyloxy)-benzoate수율 43.3%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

0.2 g of N,N'-dicyclohexylcarbodiimide is added at room temperature while stirring to a solution of 0.6 g of 2,5-bis(4-[6-acryloyloxyhexyloxy]-phenylcarbonyloxy)-benzoic acid, 0.4 g [4-(4-[6-acryloyloxyhexyloxy]-phenylcarbonyloxy)phenyl]methanol and 0.04 g of 4-dimethylaminopyridine in 20 ml of dichloromethane. The reaction mixture is stirred at room temperature overnight, poured into 100 ml of water and then extracted three times with 50 ml of dichloromethane each time. The combined organic phases are washed twice with 100 ml of water each time, dried over magnesium sulphate, filtered and the filtrate is subsequently concentrated. Chromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 1:1) and two-fold recrystallization from acetone of the fractions which are pure according to thin-layer chromatography gives 0.4 g of [4-(4-[6-acryloyloxyhexyloxy]-phenylcarbonyloxy)-phenyl]-methyl 2,5-bis(4-[6-acryloyloxyhexyloxy]-phenylcarbonyloxy)-benzoate.

후처리

  1. extractionextracted three times with 50 ml of dichloromethane each time
  2. washThe combined organic phases are washed twice with 100 ml of water each time
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate is subsequently concentrated
  6. customChromatographic purification of the residue on silica gel
  7. customwith hexane/ethyl acetate (vol. 1:1) and two-fold recrystallization from acetone of the fractions which

출처 및 근거

ORD 기록
ord-1ded68d828694b41a503d2a96b5cbdee
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05593617

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