1,1-dibutyl-4-hydroxy-2(1H)-naphthalenone → 2-[bis(methylsulfanyl)methylene]-4,4-dibutyl-1,3(2H,4H)-naphthalenedione

HRID 494455ノート

反応式

HRID 494455 の反応式
[CH2:1]([C:5]1([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[CH:7][C:6]1=[O:16])[CH2:2][CH2:3][CH3:4].COS([O-])(=O)=O.[CH3:27][S:28][C:29](=[S+]C)[S:30][CH3:31]>O1CCOCC1>[CH3:27][S:28][C:29]([S:30][CH3:31])=[C:7]1[C:6](=[O:16])[C:5]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:1][CH2:2][CH2:3][CH3:4])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:15]

参加物

4

反応物 2

HCID 688724791,1-dibutyl-4-hydroxy-2(1H)-naphthalenoneHCID 86598019[bis(methylsulfanyl)methylene](methyl)sulfonium Methyl Sulfate

生成物 1

HCID 112111042-[bis(methylsulfanyl)methylene]-4,4-dibutyl-1,3(2H,4H)-naphthalenedione

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 the product of Example 5B (25 mg, 0.092 mmol) in dioxane (4 mL) was treated with the product of Example 5A (71 mg, 0.27 mmol) and stirred at 100° C. for 2 hours, cooled to 25° C., diluted with ice water and extracted with ethyl acetate (3×). The combined organic layers were washed with water (3×) and saturated sodium chloride solution, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound. 1H NMR (300 MHz, DMSO-d6): δ 8.05 (m, 1 H), 7.66 (m, 1 H), 7.56 (d, J=7.72 Hz, 1 H), 7.43 (t, J=6.80 Hz, 1 H), 2.51 (m, 6 H), 2.10 (m, 2 H), 1.82 (m, 2 H), 1.09 (m, 4 H), 0.69 (m, 10 H).

後処理

  1. temperaturecooled to 25° C.
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic layers were washed with water (3×) and saturated sodium chloride solution
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-31b6de896dda4e9894820c69ddd5a19d
出典データセット
uspto-grants-2009_05
特許番号
US07538105B2

反応ノート

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