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

HRID 1363308노트

반응식

HRID 1363308 반응식
[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

참가 물질

5

반응물 2

HCID 82029Methyl morpholine oxideHCID 17806677HCID 17806677, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 178419074HCID 178419074, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-484b070c341b48fc9be11fc855dd1bda
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07884124B2

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