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Ethyl Acetate → HCID 57070981, 화합물

HRID 1197044
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HRID 1197044 반응식
[CH3:1][S:2][C:3]1[C:4](=[O:35])[CH:5]([CH:24](O)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH:6]([CH:8]=[CH:9][CH:10]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:7]=1.CN(C1C=CC=CN=1)C.CS(Cl)(=O)=O.C(OCC)(=O)C>ClCCl>[CH3:1][S:2][C:3]1[C:4](=[O:35])[C:5](=[CH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH:6]([CH:8]=[CH:9][CH:10]([O:16][Si:17]([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:19])[CH3:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 572430522-Methylthio-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone

생성물 1

HCID 57070981HCID 57070981, 화합물수율 64.2%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

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온도
0 °C

실험 절차

To a solution of 3.47 g of 2-methylthio-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone obtained in Example 6 in dichloromethane (30 ml) was added dimethylaminopyridine (1.54 g) and the mixture was cooled to 0° C. To the solution was dropwise added 0.59 ml of methanesulfonyl chloride, and the mixture was stirred at room temperature for 15 hours. To the reaction mixture were added ethyl acetate and an aqueous potassium hydrogensulfate, and the product was extracted into an organic layer. The extract was washed with saturated aqueous sodium hydrogencarbonate and saturated sodium chloride, dried over anhydrous magnesium sulfate, and filtered, followed by concentration. The concentrate was subjected to silica gel chromatography to give 2.15 g (yield 64%) of 2-methylthio-5-(6-methoxycarbonylhexylidene)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone.

후처리

  1. extractionan aqueous potassium hydrogensulfate, and the product was extracted into an organic layer
  2. washThe extract was washed with saturated aqueous sodium hydrogencarbonate and saturated sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationfollowed by concentration

출처 및 근거

ORD 기록
ord-dc748cbf3c3144a4a1ca071083cd8192
출처 데이터셋
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05116869

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