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

HRID 1881842노트

반응식

HRID 1881842 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:10]([CH2:15][CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:11](=[O:14])[CH:12]=[CH2:13])[CH:5]=[CH:6][C:7]=1[S:8][CH3:9].C(O)C.O1CCCC1.[CH3:30][C:31]1([CH3:44])[O:35][CH:34]([C:36]2[CH:37]=[CH:38][C:39]([CH:42]=[O:43])=[N:40][CH:41]=2)[CH2:33][O:32]1>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:30][C:31]1([CH3:44])[O:35][CH:34]([C:36]2[CH:37]=[CH:38][C:39]([C:42](=[O:43])[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([C:4]3[CH:5]=[CH:6][C:7]([S:8][CH3:9])=[C:2]([F:1])[CH:3]=3)[CH2:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[N:40][CH:41]=2)[CH2:33][O:32]1

참가 물질

8

반응물 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 469414405-(2,2-Dimethyl-1,3-dioxolan-4-yl)pyridine-2-carbaldehydeHCID 593314814-[3-fluoro-4-(methylsulfanyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

생성물 1

HCID 593314311-[5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridin-2-yl]-5-[3-fluoro-4-(methylsulfanyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione수율 71%

시약·촉매·용매 3

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

실험 절차

To a solution of 4-[3-fluoro-4-(methylsulfanyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (430 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 (290 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (41.0 mg) and triethylamine (84 μL), and the mixture was stirred with heating under reflux under argon atmosphere for 4 hr. 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 (510 mg, yield 71%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS: 516 (MH+).

후처리

  1. temperaturewith heating
  2. temperatureunder reflux under argon atmosphere for 4 hr
  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-56c4477b3fad408c8ccf732a41ba8b26
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318746B2

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