Ethyl Acetate → 2-[(2-Chloro-6-nitrophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone

HRID 2308899Notes

Reaction equation

HRID 2308899 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[CH2:4]Br.[CH3:13][C:14]1([CH3:20])[CH2:18][O:17][NH:16][C:15]1=[O:19].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(#N)C.O1CCOCCOCCOCCOCCOCC1>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[CH2:4][N:16]1[C:15](=[O:19])[C:14]([CH3:20])([CH3:13])[CH2:18][O:17]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 918582-(Bromomethyl)-1-chloro-3-nitrobenzeneHCID 6421514,4-Dimethyl-1,2-oxazolidin-3-one

Product 1

HCID 139349442-[(2-Chloro-6-nitrophenyl)methyl]-4,4-dimethyl-3-isoxazolidinoneYield 52.7%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-chloro-6-nitrobenzyl bromide (17.5 g, 0.07 mole), 4,4-dimethyl-3-isoxazolidinone (11.5 g, 0.1 mole), potassium carbonate (13.8 g, 0.1 mole), and 1,4,7,10,13,16-hexaoxacyclooctadecane (0.5 g, 0.002 mole) in acetonitrile (500 ml) was stirred at ambient temperature overnight. The reaction mixture was poured into ethyl acetate (500 ml) and the mixture washed with water (3×200 ml). The dried (magnesium sulfate) ethyl acetate layer was concentrated under reduced pressure to yield a liquid. The liquid product was subjected to chromatography on silica gel, eluting with 1:9 ethyl acetate:heptane. The appropriate fractions were combined and concentrated under reduced pressure to yield a white solid. The solid was recrystallized from ethyl acetate to yield 10.5 g of 2-[(2-chloro-6-nitrophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone, m.p. 86°-88° C.

Workup

  1. washthe mixture washed with water (3×200 ml)
  2. dry with materialThe dried (magnesium sulfate) ethyl acetate layer
  3. concentrationwas concentrated under reduced pressure
  4. customto yield a liquid
  5. washeluting with 1:9 ethyl acetate
  6. concentrationconcentrated under reduced pressure
  7. customto yield a white solid
  8. customThe solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-72a1f803fa9f4c17acf7237769c045bd
Source dataset
uspto-grants-1987_09
Patent number
US04692182

Reaction notes

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