Ethyl Acetate → HCID 70874088, compound

HRID 2208924Notes

Reaction equation

HRID 2208924 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:23][CH2:24][O:25][CH3:26].C(OCC)(=O)C>C(#N)C.O>[CH3:26][O:25][CH2:24][CH2:23][O:1][C:2]1[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 23009748Methyl 5-hydroxy-2-methyl-3-nitrobenzoate

Product 1

HCID 70874088HCID 70874088, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To stirred solution of methyl 5-hydroxy-2-methyl-3-nitrobenzoate (1.50 g, 7.61 mmol) in ACN (15 mL) was added cesium carbonate (4.96 g, 15.2 mmol) and 1-bromo-2-methoxyethane (1.57 g, 11.4 mmol). The resulting reaction mixture was heated at 80° C. overnight. On completion, the reaction mixture was diluted with water and extraction was carried out using ethyl acetate. The combined organic layers were washed with water, dried, and concentrated under reduced pressure. The crude material was purified by column chromatography to afford the title compound (1.3 g, 68).

Workup

  1. customThe resulting reaction mixture
  2. washThe combined organic layers were washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-57a79f6d19294b35a6fdc2751e303c69
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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