Ethanol → HCID 18794798, compound

HRID 1004184Notes

Reaction equation

HRID 1004184 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22](=[N+]=[N-])[C:23]([O:25][CH3:26])=[O:24])=[CH:17][CH:16]=1)[CH3:11].[CH2:29]([OH:31])[CH3:30]>CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh].C1C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH:22]([O:31][CH2:29][CH3:30])[C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:20]=1)[CH3:11]

Participants

5

Reactant 2

HCID 702EthanolHCID 53777669HCID 53777669, compound

Product 1

HCID 18794798HCID 18794798, compound

Reagents, catalysts & solvents 2

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 241BenzeneSolvent

Procedure

Rhodium (II) acetate dimer (33 mg) was added to a mixture of methyl 3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-diazopropanoate (2.80 g), ethanol (2.16 mL) and benzene (50 mL). The mixture was stirred at room temperature under a nitrogen atmosphere for 15 minutes, heated at reflux for a further 15 minutes, then cooled and evaporated in vacuo. The residue was chromatographed on silica gel using 1.5% methanol in dichloromethane as eluent to afford the title compound as a gum.

Workup

  1. temperatureheated
  2. temperatureat reflux for a further 15 minutes
  3. temperaturecooled
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel using 1.5% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-b319e990e5824fa481851db24345768c
Source dataset
uspto-grants-2000_04
Patent number
US06048883

Reaction notes

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