Allyl bromide → HCID 67439912, compound

HRID 1664226Notes

Reaction equation

HRID 1664226 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH:10]=1)[C:5]([OH:7])=[O:6].[H-].[Na+].[CH2:19](Br)[CH:20]=[CH2:21].O.[OH-].[Li+]>CN(C=O)C.O>[CH2:21]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH:10]=1)[C:5]([OH:7])=[O:6])[CH:20]=[CH2:19]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 168937Lithium hydroxide, monohydrateHCID 222530273-Hydroxy-5-(2-oxopyrrolidin-1-yl)benzoic acid

Product 1

HCID 67439912HCID 67439912, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To the solution of 1.57 g (7.1 mmol) 3-hydroxy-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid in 5 ml DMF are added 1.02 g (21.3 mmol, 3 eq) 50% sodium hydride in oil. After gas evolution stops 2.53 ml (28.4 mmol, 4 eq) allylbromide are added and the reaction mixture is stirred 4 days at 60° C. The reaction is diluted with water and extracted with EtOAc. The organic layer is dried over sodium sulfate and the solvent is evaporated at reduced pressure. The resulting ester is redissolved in 40 ml MeOH and 0.347 g (8.2 mmol, 1.2 eq) lithiumhydroxide monohydrate are added. The reaction is stirred at rt for 48 h. After evaporation of part of the solvent at reduced pressure the reaction is taken into water and washed with EtOAc. The aqueous layer is acidified with potassium hydrogensulfate and extracted with EtOAc. Drying over sodium sulfate and evaporation of the solvent at reduced pressure gives the product.

Workup

  1. additionare added
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. customthe solvent is evaporated at reduced pressure
  5. dissolutionThe resulting ester is redissolved in 40 ml MeOH
  6. stirringThe reaction is stirred at rt for 48 h
  7. customAfter evaporation of part of the solvent at reduced pressure the reaction
  8. washwashed with EtOAc
  9. extractionextracted with EtOAc
  10. dry with materialDrying over sodium sulfate and evaporation of the solvent at reduced pressure
  11. customgives the product

Sources & evidence

ORD record
ord-e2ce0c4bb2e84c7fb75476dc744d99fc
Source dataset
uspto-grants-2011_10
Patent number
US08039455B2

Reaction notes

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