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Ethanol → 1-(5-Chloro-2-thiazolyl)-5-[5-(methylthio)-2-pyridinyl]-6-(tetrahydro-2H-pyran-4-yl)-1,4-hexanedione

HRID 1881943
ノート
印刷プレビュー

反応式

HRID 1881943 の反応式
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:10](=[O:13])[CH:11]=[CH2:12])=[N:7][CH:8]=1.C(O)C.O1CCCC1.[Cl:29][C:30]1[S:34][C:33]([CH:35]=[O:36])=[N:32][CH:31]=1>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)(=O)C.C(N(CC)CC)C>[Cl:29][C:30]1[S:34][C:33]([C:35](=[O:36])[CH2:12][CH2:11][C:10](=[O:13])[CH:9]([C:6]2[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][N:7]=2)[CH2:14][CH:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)=[N:32][CH:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 441196125-Chlorothiazole-2-carbaldehydeHCID 593313384-[5-(methylsulfanyl)pyridin-2-yl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

生成物 1

HCID 593315881-(5-Chloro-2-thiazolyl)-5-[5-(methylthio)-2-pyridinyl]-6-(tetrahydro-2H-pyran-4-yl)-1,4-hexanedione収率 77%

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 4-[5-(methylsulfanyl)pyridin-2-yl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (85.0 mg) in a mixed solvent of ethanol (1.5 mL) and tetrahydrofuran (1.5 mL) were added 5-chloro-1,3-thiazole-2-carbaldehyde (86.0 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (7.9 mg) and triethylamine (16.3 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 (98.4 mg, yield 77%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, 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-97a4ed661a084eefa196192adadb58ec
出典データセット
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08318746B2

反応ノート

読み込み中…

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