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

HRID 494539
ノート
印刷プレビュー

反応式

HRID 494539 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane
溶媒

反応条件

温度
100 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-62f3b35d5e8547a291fa3a506981ed0b
出典データセット
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07538105B2

反応ノート

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