Ethanol → 1-[5-(1-hydroxy-2-methoxyethyl)-1,3-thiazol-2-yl]-5-[5-(methylsulfanyl)pyridin-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

HRID 1881942ノート

反応式

HRID 1881942 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.[OH:29][CH:30]([C:34]1[S:38][C:37]([CH:39]=[O:40])=[N:36][CH:35]=1)[CH2:31][O:32][CH3:33]>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)(=O)C.C(N(CC)CC)C>[OH:29][CH:30]([C:34]1[S:38][C:37]([C:39](=[O:40])[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:36][CH:35]=1)[CH2:31][O:32][CH3:33]

参加物

8

反応物 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 593313384-[5-(methylsulfanyl)pyridin-2-yl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-oneHCID 593316105-(1-Hydroxy-2-methoxyethyl)-1,3-thiazole-2-carbaldehyde

生成物 1

HCID 593315031-[5-(1-hydroxy-2-methoxyethyl)-1,3-thiazol-2-yl]-5-[5-(methylsulfanyl)pyridin-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione収率 37.3%

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 (168 mg) in a mixed solvent of ethanol (1.5 mL) and tetrahydrofuran (1.5 mL) were added 5-(1-hydroxy-2-methoxyethyl)-1,3-thiazole-2-carbaldehyde (119 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (15.5 mg) and triethylamine (32.1 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 (103 mg, yield 37%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (19:1, 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-39b5802d98624da09a6c66d6ebfc9b5a
出典データセット
uspto-grants-2012_11
特許番号
US08318746B2

反応ノート

読み込み中…