7-Methyl-9,10-dihydroacephenanthrene → 7-Methylacephenanthrylene

HRID 36631

반응식

HRID 36631 반응식
[CH3:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:17]4[C:8](=[CH:9][CH:10]=[CH:11][C:12]=4[C:13]=2[CH2:14][CH2:15][CH:16]=1)[CH2:7][CH2:6]3>O1CCOCC1.C(OCC)(=O)C.O>[CH3:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:3]=1[CH:4]=[C:5]1[C:17]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]2=3)[CH:7]=[CH:6]1

참가 물질

5

반응물 1

HCID 233640227-Methyl-9,10-dihydroacephenanthrene

생성물 1

HCID 149320397-Methylacephenanthrylene수율 57%

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

A solution of 7-methyl-9,10-dihydroacephenanthrene (0.13 g, 0.59 mmol) and dichlorodicyanoquinone (0.27 g, 1.18 mmol) in dioxane (10 ml) was heated at reflux for 0.5 h. The reaction mixture was allowed to cool and was diluted with ethyl acetate (50 mL) and water (20 mL). The organic layer was separated, washed with water (3×20 mL) and brine solution (3×20 mL), dried (MgSO4), and concentrated under reduced pressure. The resulting solid was purified by flash chromatography to give 0.07 g (57%) of the product: 1H NMR (CDCl3, 300 MHz) δ 8.54 (d, 1H, J=8.0 Hz), 8.40 (dd, 1H, J=7.3, 6.9 Hz), 8.24 (s, 1H), 7.66 (m, 2H), 7.58 (dd, 1H, J=8.4, 7.3 Hz), 7.46 (d, 1H, J=7.3 Hz), 7.20 (d, 1H, J= 5.1 Hz), 7.16 (d, 1H, J=5.4 Hz), 2.82 (s, 3H).

후처리

  1. temperatureat reflux for 0.5 h
  2. temperatureto cool
  3. customThe organic layer was separated
  4. washwashed with water (3×20 mL) and brine solution (3×20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting solid was purified by flash chromatography

출처 및 근거

ORD 기록
ord-bce723b98280443fb7ed47abb8f261cf
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05416089

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