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

HRID 1881889
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HRID 1881889 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:13](=[O:16])[CH:14]=[CH2:15])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[OH:24][CH:25]([C:27]1[S:31][C:30]([CH:32]=[O:33])=[N:29][CH:28]=1)[CH3:26].C(N(CC)CC)C.O1CCCC1>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:13](=[O:16])[CH2:14][CH2:15][C:32]([C:30]2[S:31][C:27]([CH:25]([OH:24])[CH3:26])=[CH:28][N:29]=2)=[O:33])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 593312984-[3-chloro-4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-oneHCID 593313835-(1-Hydroxyethyl)-1,3-thiazole-2-carbaldehyde

생성물 1

HCID 593313595-[3-chloro-4-(methylsulfonyl)phenyl]-1-[5-(1-hydroxyethyl)-1,3-thiazol-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione수율 81.8%

시약·촉매·용매 2

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

실험 절차

A mixture of 4-[3-chloro-4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (0.56 g), 5-(1-hydroxyethyl)-1,3-thiazole-2-carbaldehyde (0.30 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (43 mg), triethylamine (0.09 mL), tetrahydrofuran (4 mL) and ethanol (4 mL) was stirred with heating under reflux for 3 hr. The reaction mixture was concentrated, the residue was subjected to basic silica gel column chromatography, and eluted with ethyl acetate, and the fraction was concentrated. The residue was subjected to silica gel column chromatography, and the title compound (0.66 g, yield 81%) was obtained as a pale-yellow oil from a fraction eluted with ethyl acetate. MS: 514 (MH+).

후처리

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

출처 및 근거

ORD 기록
ord-0bd6fc809dd64896bbd5a1d9a501a7f6
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08318746B2

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