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Pyridine → HCID 86745875, 화합물

HRID 1587138
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HRID 1587138 반응식
[Si]([O:8][CH:9]([CH2:37][CH2:38][CH2:39][O:40][Si](C(C)(C)C)(C)C)/[CH:10]=[CH:11]/[CH:12]=[C:13]1[C:17](=[O:18])[C:16]([S:19][CH3:20])=[CH:15][C:14]1([CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[O:21][Si](C)(C)C)(C(C)(C)C)(C)C.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(#N)C>[OH:8][CH:9]([CH2:37][CH2:38][CH2:39][OH:40])/[CH:10]=[CH:11]/[CH:12]=[C:13]1[C:17](=[O:18])[C:16]([S:19][CH3:20])=[CH:15][C:14]1([OH:21])[CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 86745876HCID 86745876, 화합물

생성물 1

HCID 86745875HCID 86745875, 화합물수율 83.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 660 mg of 5-[(E)-4,7-bis(t-butyldimethylsilyloxy)-2-heptenylidene]-2-methylthio-4-(4-phenoxybutyl)-4-trimethylsilyloxy-2-cyclopentenone obtained in Example 570 dissolved in 50 ml of acetonitrile was added 4 ml of pyridine, under ice-cooling and stirring. A hydrogen-pyridine solution (2 ml) was added, and the mixture was stirred at 0° C. for 24 hours. The reaction mixture was poured onto saturated aqueous sodium hydrogencarbonate, and the mixture was extracted 3 times with ethyl acetate. The organic layers were combined, washed with saturated sodium chloride and dried over anhydrous magnesium sulfate. After filtration and concentration, the concentrate was subjected to silica gel column chromatography to give 320 mg (yield 83%) of 5-[(E)-4,7-dihydroxy-2-heptenylidene]-4-hydroxy-2-methylthio-4-(4-phenoxybutyl)-2-cyclopentenone.

후처리

  1. temperatureunder ice-cooling
  2. stirringthe mixture was stirred at 0° C. for 24 hours
  3. extractionthe mixture was extracted 3 times with ethyl acetate
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration and concentration

출처 및 근거

ORD 기록
ord-c1c1373a5d1949e99f4d75235b2fcc15
출처 데이터셋
uspto-grants-1993_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05216183

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