Water → HCID 131729808, compound

HRID 1511608Notes

Reaction equation

HRID 1511608 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[NH:5][CH2:6][CH2:7][C:8]1[O:9][C:10]([CH3:13])=[CH:11][CH:12]=1)[CH3:2].[H-].[Na+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].O>CN(C=O)C>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][N:5]([C:4]([O:3][CH2:1][CH3:2])=[O:14])[CH2:6][CH2:7][C:8]1[O:9][C:10]([CH3:13])=[CH:11][CH:12]=1)[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 131729807HCID 131729807, compound

Product 1

HCID 131729808HCID 131729808, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl[2-(5-methylfuran-2-yl)ethyl]carbamate (0.60 g) prepared in the step 3 was dissolved in 6 mL of DMF, 0.15 g of 60% sodium hydride was slowly added thereto with stirring and ice-cooling and the mixture was stirred at room temperature for 1 hour more. Ethyl bromoacetate (0.40 g) was slowly dropped into the reaction solution under cooling with ice and the mixture was made back to room temperature followed by stirring overnight. The reaction solution was poured over 20 mL of water followed by extracting with diethyl ether. The organic layer was 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 0.65 g of the objective compound as pale yellow liquid.

Workup

  1. temperatureice-cooling
  2. stirringthe mixture was stirred at room temperature for 1 hour more
  3. temperatureunder cooling with ice
  4. customwas made back to room temperature
  5. stirringby stirring overnight
  6. extractionby extracting with diethyl ether
  7. washThe organic layer was washed with water
  8. dry with materiala saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5e6b3dd4f4f2486c876c77c5808fcea9
Source dataset
uspto-grants-2012_07
Patent number
US08217031B2

Reaction notes

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