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 1881946ノート

反応式

HRID 1881946 の反応式
[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]

参加物

8

反応物 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

生成物 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-dione収率 95%

試薬・触媒・溶媒 3

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride触媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e1374eddd4f44f478676848da9da1f18
出典データセット
uspto-grants-2012_11
特許番号
US08318746B2

反応ノート

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