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

HRID 1363308ノート

反応式

HRID 1363308 の反応式
[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

参加物

5

反応物 2

HCID 82029Methyl morpholine oxideHCID 17806677HCID 17806677、化合物

生成物 1

HCID 111269641-benzyl-1H-pyrrole-2-carbaldehyde収率 69%

試薬・触媒・溶媒 2

HCID 178419074HCID 178419074、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-484b070c341b48fc9be11fc855dd1bda
出典データセット
uspto-grants-2011_02
特許番号
US07884124B2

反応ノート

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