Dimethyl Sulfoxide → 2,6-dibromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene

HRID 505845ノート

反応式

HRID 505845 の反応式
[Br:1][C:2]1[CH:15]=[C:14]2[CH2:16][C:11]3[C:12]4=[C:13]2[C:4](=[CH:5][CH:6]=[C:7]4[CH:8]=[C:9]([Br:17])[CH:10]=3)[CH:3]=1.CC([O-])(C)C.[K+].CS(C)=O.CN(P(N(C)C)(N(C)C)=O)C>C(Cl)Cl.O>[Br:1][C:2]1[CH:15]=[C:14]2[CH2:16][C:11]3[C:12]4[C:13]2=[C:4]([CH2:5][CH2:6][C:7]=4[CH:8]=[C:9]([Br:17])[CH:10]=3)[CH:3]=1

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 12679HexamethylphosphoramideHCID 23665647Potassium tert-butoxideHCID 594310762,6-dibromo-4H-cyclopenta[def]phenanthrene

生成物 1

HCID 125243672,6-dibromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene収率 133.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

2,6-dibromo-4H-cyclopenta[def]phenanthrene (2.6 g, 7.7 mmol), t-BuOK(20.8 g, 61.6 mmol), DMSO(20 ml), and HMPA(20 ml) was placed in 50 ml round bottom flask with a syringe. The mixture was stirred for 50 minutes at room temperature and cooled to 0° C. CH3l(3.75 ml, 61.6 mmol) was dropped to the mixture with a syringe and the resultant solution was stirred for 30 minutes at 0° C. Then, water(50 ml) and methylene chloride(50 ml) were added to the solution to separate an organic layer. The organic layer was purified by silica gel column chromatography to obtain compound 2(3.6 g, 80%). 1H NMR (300 MHz, CDCl3, δ): 7.98(2H, s), 7.79(2H, s), 7.73(2H, s), 1.93(m, 6H).

後処理

  1. temperaturecooled to 0° C
  2. additionCH3l(3.75 ml, 61.6 mmol) was dropped to the mixture with a syringe
  3. customto separate an organic layer
  4. customThe organic layer was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-b6dc059a8aca4870ac08acd0494ee8a1
出典データセット
uspto-grants-2010_08
特許番号
US07781579B2

反応ノート

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