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Ethanol → 5-methyl-5-[5-(methylsulfanyl)pyridin-2-yl]-1-(pyridin-2-yl)-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

HRID 1881941
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HRID 1881941 반응식
[CH3:1][C:2]([C:14]1[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][N:15]=1)([CH2:7][CH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[C:3](=[O:6])[CH:4]=[CH2:5].C(O)C.O1CCCC1.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH:36]=[O:37]>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:1][C:2]([C:14]1[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][N:15]=1)([CH2:7][CH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1)[C:3](=[O:6])[CH2:4][CH2:5][C:36]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=1)=[O:37]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 142732-PyridinecarboxaldehydeHCID 593315004-methyl-4-[5-(methylsulfanyl)pyridin-2-yl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

생성물 1

HCID 593314515-methyl-5-[5-(methylsulfanyl)pyridin-2-yl]-1-(pyridin-2-yl)-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione수율 58%

시약·촉매·용매 3

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride촉매
HCID 8471Triethylamine용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-methyl-4-[5-(methylsulfanyl)pyridin-2-yl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (77.8 mg) in a mixed solvent of ethanol (0.6 mL) and tetrahydrofuran (0.6 mL) were added pyridine-2-carbaldehyde (48.5 μL), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (6.9 mg) and triethylamine (14.2 μL), and the mixture was stirred with heating under reflux for 3 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (60.7 mg, yield 58%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio).

후처리

  1. temperaturewith heating
  2. temperatureunder reflux for 3 hr
  3. washwashed with water
  4. dry with materialThe ethyl acetate layer was dried (MgSO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e628f3671eef4733ab01d575153a0c54
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08318746B2

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