Sodium hydride → HCID 53816239, compound

HRID 1723184Notes

Reaction equation

HRID 1723184 reaction equation
[O:1]=[C:2]1[CH:6]([CH2:7][CH2:8][CH3:9])[C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[O:3]1.[H-].[Na+].Br[CH2:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>CN(C)C=O>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][C:6]1([CH2:7][CH2:8][CH3:9])[C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[O:3][C:2]1=[O:1])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 62576Benzyl bromoacetateHCID 118195622(3H)-Benzofuranone, 3-propyl-

Product 1

HCID 53816239HCID 53816239, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 0.204 mol of 2,3-dihydro-2-oxo-3-propylbenzofuran in 200 ml of anhydrous dimethylformamide is added to a suspension of 0.204 mol of sodium hydride in 100 ml of anhydrous dimethylformamide. The medium is maintained with stirring at room temperature for one hour, 0.224 mol of benzyl bromoacetate is then added and the medium is left for 12 hours at room temperature. The reaction mixture is concentrated under vacuum and hydrolyzed using one liter of water, the aqueous phase is extracted with twice 250 ml of benzene, the organic phase dried over anhydrous sodium sulfate and the solvent evaporated off. The crystallized residue is washed with isopropyl ether and filtered, yielding 0.173 mol of a pale yellow oil.

Workup

  1. temperatureThe medium is maintained
  2. waitthe medium is left for 12 hours at room temperature
  3. concentrationThe reaction mixture is concentrated under vacuum
  4. extractionthe aqueous phase is extracted with twice 250 ml of benzene
  5. dry with materialthe organic phase dried over anhydrous sodium sulfate
  6. customthe solvent evaporated off
  7. washThe crystallized residue is washed with isopropyl ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-32c2043be1fc4325bad3ba8d8995c7ca
Source dataset
uspto-grants-1989_08
Patent number
US04859700

Reaction notes

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