Sodium hydride → HCID 14303492, compound

HRID 476572Notes

Reaction equation

HRID 476572 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[CH:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[CH:17]=1.[H-].[Na+].Br[CH2:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>CN(C)C=O>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][C:7]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]2[CH:17]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:9][C:8]1=[O:10])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 62576Benzyl bromoacetateHCID 28767462(3H)-Benzofuranone, 5-chloro-3-phenyl-

Product 1

HCID 14303492HCID 14303492, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 0.204 mol of 5-chloro-2,3-dihydro-2-oxo-3-phenylbenzofuran 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 slowly 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 extracted with twice 250 ml of benzene, the organic phase dried over anhydrous sodium sulfate and the solvent evaporated off. The residue is washed with isopropyl ether and then filtered. 0.173 mol is thereby obtained.

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 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 residue is washed with isopropyl ether
  8. filtrationfiltered
  9. custom0.173 mol is thereby obtained

Sources & evidence

ORD record
ord-30d1c342f6534bdf90589baa2ea64ae7
Source dataset
uspto-grants-1989_12
Patent number
US04885299

Reaction notes

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