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

HRID 1363308Notes

Reaction equation

HRID 1363308 reaction equation
[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

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 17806677HCID 17806677, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-484b070c341b48fc9be11fc855dd1bda
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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