Potassium Hydroxide → HCID 68410994, compound

HRID 1511609Notes

Reaction equation

HRID 1511609 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][N:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:7][CH2:8][C:9]1[O:10][C:11]([CH3:14])=[CH:12][CH:13]=1)C.[OH-].[K+]>C(O)C>[CH2:18]([O:17][C:15]([N:6]([CH2:5][C:4]([OH:20])=[O:3])[CH2:7][CH2:8][C:9]1[O:10][C:11]([CH3:14])=[CH:12][CH:13]=1)=[O:16])[CH3:19]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 131729808HCID 131729808, compound

Product 1

HCID 68410994HCID 68410994, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl{ethoxycarbonyl[2-(5-methylfuran-2-yl)ethyl]-amino}acetate (0.65 g) prepared in the step 4 was dissolved in 5 mL of ethanol, 0.30 g of potassium hydroxide was added thereto and the mixture was heated to reflux for 3 hours. The solvent of the reaction solution was evaporated in vacuo and the residue was dissolved in ethyl acetate. The resulting solution was slowly neutralized with 1N aqueous solution of hydrochloric acid (ca. 80 mL) with stirring to adjust to pH 3. The organic layer was separated, washed with water and a saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom in vacuo. The residue was purified by silica gel column chromatography to give 0.18 g of the objective compound as yellow liquid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe solvent of the reaction solution was evaporated in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materiala saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-03c0af76999c47dc97ba93d868a5549a
Source dataset
uspto-grants-2012_07
Patent number
US08217031B2

Reaction notes

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