Ethanol → HCID 22403807, compound

HRID 259816Notes

Reaction equation

HRID 259816 reaction equation
[CH3:1][O:2][C:3]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][CH:20]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])[O:19][C:18]3=[O:27])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[H-].[Na+].[CH2:30](O)C>C(OCC)C>[CH2:1]([O:2][C:3]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[CH:12]=[CH:13][C:14]([N:17]3[CH2:21][CH:20]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])[O:19][C:18]3=[O:27])=[CH:15][CH:16]=2)=[CH:5][CH:4]=1)[CH3:30]

Participants

5

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 476911HCID 476911, compound

Product 1

HCID 22403807HCID 22403807, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A slurry of (±)-N-[[3-[4-(4-methoxy-5-oxo-1,3,6-cycloheptatrien-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (0.100 g, 0.27 mmol) in absolute ethanol (10 mL) was treated with a catalytic quantity of sodium hydride (5 mg of a 60% dispersion in mineral oil). The mixture was heated to reflux under nitrogen, during which time the mixture became a homogeneous solution. After 15 min of reflux the solution was cooled to ambient temperature and a solid precipitate noted. The reaction mixture was diluted with diethyl ether and the solids collected by filtration. After drying in vacuo, 0.088 g (85%) of the title compound was obtained as a light yellow solid with the following characteristics:

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under nitrogen, during which time the mixture
  3. temperatureAfter 15 min of reflux the solution
  4. filtrationthe solids collected by filtration
  5. customAfter drying in vacuo

Sources & evidence

ORD record
ord-3c1dea8c913e48f0a49e14f4f50a2023
Source dataset
uspto-grants-1996_06
Patent number
US05523403

Reaction notes

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