Ethanol → 5-[3-chloro-4-(methylsulfonyl)phenyl]-1-[5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridin-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

HRID 1881843노트

반응식

HRID 1881843 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].C(O)C.O1CCCC1.[CH3:32][C:33]1([CH3:46])[O:37][CH:36]([C:38]2[CH:39]=[CH:40][C:41]([CH:44]=[O:45])=[N:42][CH:43]=2)[CH2:35][O:34]1>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)(=O)C.C(N(CC)CC)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:44]([C:41]2[CH:40]=[CH:39][C:38]([CH:36]3[CH2:35][O:34][C:33]([CH3:46])([CH3:32])[O:37]3)=[CH:43][N:42]=2)=[O:45])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

참가 물질

8

반응물 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 469414405-(2,2-Dimethyl-1,3-dioxolan-4-yl)pyridine-2-carbaldehydeHCID 593312984-[3-chloro-4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

생성물 1

HCID 593316195-[3-chloro-4-(methylsulfonyl)phenyl]-1-[5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridin-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione수율 78.4%

시약·촉매·용매 3

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride촉매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-[3-chloro-4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (500 mg) in a mixed solvent of ethanol (3 mL) and tetrahydrofuran (3 mL) were added 5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridine-2-carbaldehyde (320 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (42.0 mg) and triethylamine (84 μL), and the mixture was stirred with heating under reflux for 4 hr under argon atmosphere. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (620 mg, yield 78%) was obtained as a pale-brown amorphous solid from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). MS: 566 (MH+).

후처리

  1. temperaturewith heating
  2. temperatureunder reflux for 4 hr under argon atmosphere
  3. washwashed with water
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bee728c04ce7483184c0096e5af86f66
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318746B2

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