Methyl morpholine oxide → 1-benzyl-1H-pyrrole-2-carbaldehyde

HRID 1363308Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1363308
[CH2:1]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH2:13][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:1]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 82029Methyl morpholine oxideHCID 17806677HCID 17806677, Verbindung

Produkt 1

HCID 111269641-benzyl-1H-pyrrole-2-carbaldehydeAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419074HCID 178419074, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of (1-benzyl-1H-pyrrol-2-yl)-methanol (3.08 g, 16.4 mmol) and powdered 4 Å molecular sieves (3.0 g) in DCM (33 mL) was added NMO (2.89 g, 24.7 mmol) along with tetrapropylammonium perruthenate (TPAP) (289 mg, 0.822 mmol). The mixture turned black and exothermed. After 20 min, the crude mixture was filtered through a plug of silica gel (EtOAc) to give a red solution. The solution was concentrated in vacuo and the resulting oil was chromatographed over silica gel (0 to 35% EtOAc in heptane over 35 min) to give 1-benzyl-1H-pyrrole-2-carboxaldehyde as a colorless oil (2.09 g, 69%). 1H NMR (400 MHz, CDCl3) δ (ppm) 9.58 (s, 1H) 7.24-7.35 (m, 3H) 7.16 (dd, J=7.7, 1.1 Hz, 2H) 6.98 (d, J=3.5 Hz, 2H) 6.26-6.31 (m, 1H) 5.58 (s, 2H).

Aufarbeitung

  1. filtrationthe crude mixture was filtered through a plug of silica gel (EtOAc)
  2. customto give a red solution
  3. concentrationThe solution was concentrated in vacuo
  4. customthe resulting oil was chromatographed over silica gel (0 to 35% EtOAc in heptane over 35 min)

Quellen und Nachweise

ORD-Eintrag
ord-484b070c341b48fc9be11fc855dd1bda
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07884124B2

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