Diazoethane → HCID 53995746, compound

HRID 1579005Notes

Reaction equation

HRID 1579005 reaction equation
[N+:1](=[CH:3][CH3:4])=[N-:2].[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15](Cl)=[O:16]>CCOCC>[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:13]=[C:14]([C:15](=[O:16])[C:3](=[N+:1]=[N-:2])[CH3:4])[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 70695DiazoethaneHCID 130348853-(2-Pyridinyloxy)benzoyl chloride

Product 1

HCID 53995746HCID 53995746, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of diazoethane (2.5 mol equivalent) in ether (150 ml), a solution of 3-(2-pyridyloxy)benzoyl chloride in anhydrous ether (90 ml) is added dropwise at -20°C for 40 minutes. The resultant mixture is stirred at -20°C for 20 minutes. The diazoethane is evaporated at -20°C under reduced pressure, and the ether is evaporated at -10°C to 0°C under reduced pressure. The residue is chromatographed on a column of silica gel, which is eluted with 20% ether/benzene and 30% ether/benzene to give 3-(2-pyridyloxy)-1-(2-diazopropionyl)benzene (2.87 g) as an oily substance. IR (CCl4): 2060, 1630 cm-1.

Workup

  1. customThe diazoethane is evaporated at -20°C under reduced pressure
  2. customthe ether is evaporated at -10°C to 0°C under reduced pressure
  3. customThe residue is chromatographed on a column of silica gel, which
  4. washis eluted with 20% ether/benzene and 30% ether/benzene

Sources & evidence

ORD record
ord-4519796bfd5742edb312f81acc934913
Source dataset
uspto-grants-1976_02
Patent number
US03940403

Reaction notes

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