Tetrahydrofuran → 1-[5-(1,2-dihydroxy-2-methylpropyl)-1,3-thiazol-2-yl]-5-[4-(methylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

HRID 1881893노트

반응식

HRID 1881893 반응식
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH2:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:12](=[O:15])[CH:13]=[CH2:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[OH:23][CH:24]([C:29]1[S:33][C:32]([CH:34]=[O:35])=[N:31][CH:30]=1)[C:25]([OH:28])([CH3:27])[CH3:26].C(N(CC)CC)C.O1CCCC1>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(O)C>[OH:23][CH:24]([C:29]1[S:33][C:32]([C:34](=[O:35])[CH2:14][CH2:13][C:12](=[O:15])[CH:11]([C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=2)[CH2:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[N:31][CH:30]=1)[C:25]([OH:28])([CH3:27])[CH3:26]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 593314165-(1,2-Dihydroxy-2-methylpropyl)-1,3-thiazole-2-carbaldehydeHCID 684337694-[4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

생성물 1

HCID 593312761-[5-(1,2-dihydroxy-2-methylpropyl)-1,3-thiazol-2-yl]-5-[4-(methylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione수율 62.8%

시약·촉매·용매 2

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride촉매HCID 702Ethanol용매

실험 절차

A mixture of 4-[4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (0.50 g), 5-(1,2-dihydroxy-2-methylpropyl)-1,3-thiazole-2-carbaldehyde (0.32 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (43 mg), triethylamine (0.09 mL), tetrahydrofuran (6 mL) and ethanol (6 mL) was stirred with heating under reflux for 1 hr. The reaction mixture was concentrated, the residue was subjected to basic silica gel column chromatography, and eluted with tetrahydrofuran, and the fraction was concentrated. The residue was subjected to silica gel column chromatography, and the title compound (0.51 g, yield 61%) was obtained as a colorless oil from a fraction eluted with ethyl acetate. MS: 524 (MH+).

후처리

  1. temperaturewith heating
  2. temperatureunder reflux for 1 hr
  3. concentrationThe reaction mixture was concentrated
  4. washeluted with tetrahydrofuran
  5. concentrationthe fraction was concentrated

출처 및 근거

ORD 기록
ord-4b2805bc809f4240b8c4193105356256
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318746B2

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