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Ethanol → 1-[5-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)pyridin-2-yl]-5-[4-(cyclopropylsulfonyl)phenyl]-2-methyl-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

HRID 1881849
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HRID 1881849 반응식
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21](=[O:25])[CH:22]=[CH:23][CH3:24])[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C(O)C.O1CCCC1.[Si:34]([O:41][CH:42]([C:44]1[CH:45]=[CH:46][C:47]([CH:50]=[O:51])=[N:48][CH:49]=1)[CH3:43])([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35]>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)(=O)C.C(N(CC)CC)C>[Si:34]([O:41][CH:42]([C:44]1[CH:45]=[CH:46][C:47]([C:50](=[O:51])[CH:23]([CH3:24])[CH2:22][C:21](=[O:25])[CH:13]([C:10]2[CH:9]=[CH:8][C:7]([S:4]([CH:1]3[CH2:2][CH2:3]3)(=[O:6])=[O:5])=[CH:12][CH:11]=2)[CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[N:48][CH:49]=1)[CH3:43])([C:37]([CH3:40])([CH3:38])[CH3:39])([CH3:36])[CH3:35]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 593313475-(1-{[Tert-butyl(dimethyl)silyl]oxy}ethyl)pyridine-2-carbaldehydeHCID 684311882-[4-(cyclopropylsulfonyl)phenyl]-1-(tetrahydro-2H-pyran-4-yl)hex-4-en-3-one

생성물 1

HCID 593312241-[5-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)pyridin-2-yl]-5-[4-(cyclopropylsulfonyl)phenyl]-2-methyl-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione
수율 58%

시약·촉매·용매 3

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride촉매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-[4-(cyclopropylsulfonyl)phenyl]-1-(tetrahydro-2H-pyran-4-yl)hex-4-en-3-one (180 mg) in a mixed solvent of ethanol (3 mL) and tetrahydrofuran (3 mL) were added 5-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)pyridine-2-carbaldehyde (158 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (14.7 mg) and triethylamine (29.9 μL), and the mixture was stirred with heating under reflux under argon atmosphere 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 washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (180 mg, yield 58%) was obtained as a pale-yellow oil from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS: 628 (MH+).

후처리

  1. temperaturewith heating
  2. temperatureunder reflux under argon atmosphere for 3 hr
  3. washwashed with water
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c8166407cc3a449d8d3270a8738e4e25
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08318746B2

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