Ethanol → 1-[5-(1-{[Tert-butyl(dimethyl)silyl]oxy}ethyl)pyridin-2-yl]-6-cyclopentyl-5-[5-(methylsulfanyl)pyridin-2-yl]hexane-1,4-dione

HRID 1881946노트

반응식

HRID 1881946 반응식
[CH:1]1([CH2:6][CH:7]([C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][N:13]=2)[C:8](=[O:11])[CH:9]=[CH2:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)C.O1CCCC1.[Si:28]([O:35][CH:36]([C:38]1[CH:39]=[CH:40][C:41]([CH:44]=[O:45])=[N:42][CH:43]=1)[CH3:37])([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)(=O)C.C(N(CC)CC)C>[Si:28]([O:35][CH:36]([C:38]1[CH:39]=[CH:40][C:41]([C:44](=[O:45])[CH2:10][CH2:9][C:8](=[O:11])[CH:7]([C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][N:13]=2)[CH2:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[N:42][CH:43]=1)[CH3:37])([C:31]([CH3:34])([CH3:32])[CH3:33])([CH3:30])[CH3:29]

참가 물질

8

반응물 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 593313475-(1-{[Tert-butyl(dimethyl)silyl]oxy}ethyl)pyridine-2-carbaldehydeHCID 593315425-Cyclopentyl-4-[5-(methylsulfanyl)pyridin-2-yl]pent-1-en-3-one

생성물 1

HCID 593314531-[5-(1-{[Tert-butyl(dimethyl)silyl]oxy}ethyl)pyridin-2-yl]-6-cyclopentyl-5-[5-(methylsulfanyl)pyridin-2-yl]hexane-1,4-dione수율 95%

시약·촉매·용매 3

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

실험 절차

To a solution of 5-cyclopentyl-4-[5-(methylsulfanyl)pyridin-2-yl]pent-1-en-3-one (455 mg) in a mixed solvent of ethanol (8 mL) and tetrahydrofuran (8 mL) were added 5-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)pyridine-2-carbaldehyde (878% mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (44.5 mg) and triethylamine (92.0 μL), and the mixture was stirred with heating under reflux for 2 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 (848 mg, yield 95%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio).

후처리

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

출처 및 근거

ORD 기록
ord-e1374eddd4f44f478676848da9da1f18
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318746B2

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