Triethylamine → 2-[(2-Chlorophenyl)methyl]-5-ethoxy-4,4-dimethyl-1,2-oxazolidin-3-one

HRID 1995496Notes

Reaction equation

HRID 1995496 reaction equation
Cl[CH:2]1[O:6][N:5]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[C:4](=[O:15])[C:3]1([CH3:17])[CH3:16].C(N(CC)CC)C.[O-:25][CH2:26][CH3:27].[Na+]>C(O)C>[Cl:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][N:5]1[C:4](=[O:15])[C:3]([CH3:17])([CH3:16])[CH:2]([O:25][CH2:26][CH3:27])[O:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723922Sodium ethoxideHCID 131925865-Chloro-2-[(2-chlorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one

Product 1

HCID 131925882-[(2-Chlorophenyl)methyl]-5-ethoxy-4,4-dimethyl-1,2-oxazolidin-3-oneYield 42.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 3.0 grams (0.011 mole) of 5-chloro-2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone (Example 23 (A)) in 30 ml of absolute ethanol was added dropwise 1.2 grams (0.012 mole) of triethylamine. Upon completion of addition the reaction mixture was heated under reflux for 18 hours; thin layer chromatography of the reaction mixture indicated no reaction had taken place. The reaction mixture was cooled, 0.74 gram (1 equiv.) of sodium ethoxide was added, and the reaction mixture was stirred at ambient temperature for two hours; again thin layer chromatography on the reaction mixture indicated that no reaction had taken place. The reaction mixture was filtered and diluted with 150 ml of methylene chloride. The mixture was washed with two 100-ml portions of water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give an oil residue. The oil was distilled at 80°/3.3 Pa. using a short-path distilling system. Nuclear magnetic resonance spectroscopy indicated 83% of the distillate to be the desired product. The distillate was subjected to column chromatography on silica gel, using 20% ethyl acetate in heptane for elution. The appropriate fractions were combined and concentrated under reduced pressure to give 1.3 grams of 2-[(2-chlorophenyl)methyl]-5-ethoxy-4,4-dimethyl-3-isoxazolidinone as an oil.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 18 hours
  4. temperatureThe reaction mixture was cooled
  5. filtrationThe reaction mixture was filtered
  6. additiondiluted with 150 ml of methylene chloride
  7. washThe mixture was washed with two 100-ml portions of water
  8. dry with materialThe organic layer was dried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customto give an oil residue
  12. distillationThe oil was distilled at 80°/3.3 Pa
  13. washfor elution
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5183f4841a984c67b71df37115066aa3
Source dataset
uspto-grants-1983_09
Patent number
US04405357

Reaction notes

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