Hydrogen Peroxide → HCID 58036793、化合物

HRID 1515171ノート

反応式

HRID 1515171 の反応式
[C:1]1([P:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:17]=2[NH:16][CH:15]([CH3:18])[CH:14]=[CH:13]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OO.[O-:27]S([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:19]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:17]=2[NH:16][CH:15]([CH3:18])[CH:14]=[CH:13]3)=[O:27])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

参加物

5

反応物 3

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 58036800HCID 58036800、化合物

生成物 1

HCID 58036793HCID 58036793、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 8-diphenylphosphino-2-methyl-1,2-dihydroquinoline (2) (10.5 g, 32 mmol) in CH2Cl2 (100 mL) was added H2O2 (6.6 mL, 30% w/w in H2O, 63.9 mmol) at 0° C. and the solution was stirred at room temperature for 1 hour. The solution was then cooled to 0° C., saturated aqueous Na2SO3 solution (10 mL) was added and the mixture was warmed to room temperature. Products were extracted with EtOAc, washed with water and saturated aqueous NaCl, dried (MgSO4) and evaporated to give 5 as a yellow oil (11 g, quantitative). 1H NMR (400.13 MHz, CDCl3) δ 7.7-7.6 (m, 4H, Ph-H), 7.6-7.5 (m, 2H, Ph-H), 7.5-7.4 (m, 4H, Ph-H), 6.97 (bs, 1H, N1—H), 6.87 (d, 1H, J=7.2 Hz, C5—H), 6.55 (ddd, 1H, J=14.0, 8.0, 1.6 Hz, C7—H), 6.36 (ddd, 1H, J=10.0, 7.6, 2.8 Hz, C6—H), 6.22 (d, 1H, J=10.0 Hz, C4—H), 5.51 (ddd, 1H, J=10.0, 4.0, 2.0 Hz, C3—H), 4.43 (m, 1H, C2—H), 1.17 (d, 3H, J=6.8 Hz, C1′—CH3) ppm; 13C NMR (100.61 MHz, CDCl3) δ 148.2 (d, J=5.1 Hz), 146.0 (d, J=6.1 Hz), 135.7 (d, J=8.1 Hz), 134.8, 132.4, 131.3 (d, J=5.1 Hz), 131.0 (d, J=11.1 Hz), 130.8 (d, J=10.1 Hz), 130.7 (d, J=10.1 Hz), 130.1, 129.2, 127.2 (d, J=12.1 Hz), 126.6 (d, J=13.1 Hz), 126.3, 125.0 (d, J=8.1 Hz), 124.1 (d, J=13.1 Hz), 122.8, 121.1, 119.7 (d, J=8.1 Hz), 113.6 (d, J=14.1 Hz), 107.3, 106.2, 46.9, 23.5 ppm; 31P NMR (161.97 MHz, CDCl3) δ 36.0 ppm.

後処理

  1. temperatureThe solution was then cooled to 0° C.
  2. temperaturethe mixture was warmed to room temperature
  3. extractionProducts were extracted with EtOAc
  4. washwashed with water and saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. customevaporated

出典と根拠

ORDレコード
ord-bc3d3fedd6c4436cb1da41b2ca53b124
出典データセット
uspto-grants-2012_07
特許番号
US08222415B2

反応ノート

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