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

HRID 233417ノート

反応式

HRID 233417 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1ded68d828694b41a503d2a96b5cbdee
出典データセット
uspto-grants-1997_01
特許番号
US05593617

反応ノート

読み込み中…