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Sodium Iodide → 3-(Decyloxy)-5-[[6-[2,3-bis(phenylmethoxy)phenyl]hexyl]oxy]benzoic acid (acetyloxy)methyl ester

HRID 1492869
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HRID 1492869 반응식
[CH2:1]([O:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:29]=2[O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:20]=1)[C:15]([OH:17])=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:50]([O:53][CH2:54]Cl)(=[O:52])[CH3:51].[I-].[Na+].C(N(CC)CC)C>CC(C)=O.CN(C=O)C>[C:50]([O:53][CH2:54][O:16][C:15](=[O:17])[C:14]1[CH:18]=[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH2:35][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:29]=2[O:42][CH2:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:20]=[C:12]([O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH:13]=1)(=[O:52])[CH3:51]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 69366Chloromethyl acetateHCID 189515713-(Decyloxy)-5-[[6-[2,3-bis(phenylmethoxy)phenyl]hexyl]oxy]benzoic acid

생성물 1

HCID 541636573-(Decyloxy)-5-[[6-[2,3-bis(phenylmethoxy)phenyl]hexyl]oxy]benzoic acid (acetyloxy)methyl ester수율 23.5%

시약·촉매·용매 2

HCID 180Acetone용매
HCID 6228Dimethylformamide용매

실험 절차

A mixture of 0.5 g (0.75 mmol) of 3-(decyloxy)-5-[[6-[2,3-bis (phenylmethoxy)phenyl]hexyl]oxy]benzoic acid, 0.25 g (2.25 mmol) of chloromethyl acetate, 0.23 g (1.5 mmol) of sodium iodide and 0.31 ml (2.25 mmol) of triethylamine in 15 ml of acetone and 5 ml of DMF was stirred at reflux under argon for 19 hours. The solvent was removed under reduced pressure, NaHCO3 solution was added to the residue and the product was extracted with ethyl acetate. The dried extract was concentrated to an oil which was purified by HPLC using 10% ethyl acetate-hexane to give 0.13 g of 3-(decyloxy)-5-[[6-[2,3-bis(phenylmethoxy)phenyl]hexyl]oxy]benzoic acid (acetyloxy)methyl ester as an oil. A mixture of 0.13 g of 3-(decyloxy)-5-[[6-[2,3-bis (phenylmethoxy)phenyl]hexyl]oxy]benzoic acid (acetyloxy)methyl ester and 0.1 g of 10% palladium on carbon in 15 ml of ethyl acetate was stirred under a hydrogen atmosphere for 3.5 hours when uptake ceased. The usual workup gave 0.07 g of 3-(decyloxy)-5-[[6-(2,3-dihydroxyphenyl)hexyl]oxy]benzoic acid (acetyloxy) methyl ester as an oil. The structure was confirmed by the nmr and mass spectra.

후처리

  1. temperatureat reflux under argon for 19 hours
  2. customThe solvent was removed under reduced pressure, NaHCO3 solution
  3. additionwas added to the residue
  4. extractionthe product was extracted with ethyl acetate
  5. extractionThe dried extract
  6. concentrationwas concentrated to an oil which
  7. customwas purified by HPLC

출처 및 근거

ORD 기록
ord-5842502d5cad441f9f90e9ba3d63375c
출처 데이터셋
uspto-grants-1994_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05374772

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