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

HRID 494455노트

반응식

HRID 494455 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-31b6de896dda4e9894820c69ddd5a19d
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538105B2

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