Hydrogen Peroxide → HCID 58036793, Verbindung

HRID 1952003Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1952003
[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

Komponenten

5

Edukt 3

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 58036800HCID 58036800, Verbindung

Produkt 1

HCID 58036793HCID 58036793, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-994093e5c09e42deaa738f02fb8f1936
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404843B2

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