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Pyridine → 2-[Bis(methylthio)methylene]-4-(5,5-dimethylhexyl)-4-methylnaphthalene-1,3(2h,4h)-dione

HRID 2224863
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인쇄 미리보기

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HRID 2224863 반응식
[CH3:1][C:2]([CH3:21])([CH3:20])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1([CH3:19])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[CH:9][C:8]1=[O:18].N1C=CC=CC=1.COS([O-])(=O)=O.[CH3:34][S:35][C:36](=[S+]C)[S:37][CH3:38]>O1CCOCC1>[CH3:34][S:35][C:36]([S:37][CH3:38])=[C:9]1[C:8](=[O:18])[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][C:2]([CH3:21])([CH3:20])[CH3:1])([CH3:19])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:17]
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참가 물질

5

반응물 3

HCID 1049PyridineHCID 692680301-(5,5-Dimethylhexyl)-4-hydroxy-1-methylnaphthalen-2(1h)-oneHCID 86598019[bis(methylsulfanyl)methylene](methyl)sulfonium Methyl Sulfate

생성물 1

HCID 113038662-[Bis(methylthio)methylene]-4-(5,5-dimethylhexyl)-4-methylnaphthalene-1,3(2h,4h)-dione수율 100.3%

시약·촉매·용매 1

HCID 312751,4-Dioxane
용매

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온도
100 °C

실험 절차

A solution of Example 35G (1.06 g, 3.70 mmol) and pyridine (2.40 mL, 29.6 mmol) in 1,4-dioxane (15 mL) was treated with [bis(methylsulfanyl)methylene](methyl)sulfonium methyl sulfate (3.93 g, 14.8 mmol) and stirred at 100° C. for 1 hour. The mixture was cooled to 25° C. and partitioned between ethyl acetate and water. The ethyl acetate layer was washed with water and brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane followed by 5%, 10%, and 20% ethyl acetate in hexane to give the title compound (1.45 g, 99%). 1H NMR (300 MHz, CDCl3): δ ppm 0.78 (m, 10 H) 1.01 (m, 5 H) 1.56 (m, 3 H) 1.77 (m, 1 H) 2.23 (m, 1 H) 2.56 (m, 6 H) 7.39 (m, 2 H) 7.56 (m, 1 H) 8.21 (m, 1 H). MS (ESI+) m/z 391 (M+H)+.

후처리

  1. temperatureThe mixture was cooled to 25° C.
  2. custompartitioned between ethyl acetate and water
  3. washThe ethyl acetate layer was washed with water and brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with hexane

출처 및 근거

ORD 기록
ord-39769a0664d54948814410a045e22aa3
출처 데이터셋
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07378414B2

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