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Acetic Acid → 2-Methylthio-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone

HRID 1197040
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HRID 1197040 반응식
[CH3:1][S-:2].[Na+].C(O)(=O)C.C(N(CC)CC)C.O1[CH:20]2[CH:16]1[C:17](=[O:48])[CH:18]([CH:37]([OH:47])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][CH3:46])=[O:44])[CH:19]2[CH:21]=[CH:22][CH:23]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CO.O>[CH3:1][S:2][C:16]1[C:17](=[O:48])[CH:18]([CH:37]([OH:47])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][CH3:46])=[O:44])[CH:19]([CH:21]=[CH:22][CH:23]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:20]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 4378561Sodium methanethiolateHCID 54508019HCID 54508019, 화합물

생성물 1

HCID 572430522-Methylthio-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone수율 100.4%

시약·촉매·용매 2

HCID 887
Methanol
용매
2회
HCID 962Water용매

실험 절차

A solution of sodium thiomethoxide (2.30 g) in methanol (100 ml) was cooled to 0° C., acetic acid (2.82 ml) was added, the mixture was stirred for 5 minutes, Triethylamine (915 ml) was added, and a solution of 2,3-epoxy-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)cyclopentanone (3.26 g) in methanol (40 ml) was added. After stirring at room temperature for 12 hours, water was added to the mixture, and the mixture extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and filtered, followed by concentration. The concentrate was subjected to silica gel chromatography to give 3.47 g (yield 96%) of 2-methylthio-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone.

후처리

  1. stirringAfter stirring at room temperature for 12 hours
  2. extractionthe mixture extracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationfollowed by concentration

출처 및 근거

ORD 기록
ord-5c33214236fd4aa9ac726f779b0af62a
출처 데이터셋
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05116869

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