Sodium hydride → HCID 67005342, compound

HRID 2068485Notes

Reaction equation

HRID 2068485 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[O:12])[CH2:8][C:9](=[O:11])[CH3:10].[H-].[Na+].Br[CH2:16][C:17]([O:19][CH3:20])=[O:18]>CS(C)=O>[O:11]=[C:9]([CH3:10])[CH:8]([C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:12])[CH2:16][C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 127072211-(Pyridin-2-yl)butane-1,3-dione

Product 1

HCID 67005342HCID 67005342, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Conditions

Temperature
20 °C

Procedure

A solution of 3.38 g (20.7 mmol) of 1-(pyridin-2-yl)butane-1,3-dione dissolved in dimethyl sulfoxide was slowly added dropwise to 0.911 g (22.78 mmol) of sodium hydride in 25 ml of dimethyl sulfoxide such that the temperature did not exceed 30° C. The mixture was stirred at 20° C. for another 30 minutes. 3.486 g (22.78 mmol) of methyl bromoacetate in a little dimethyl sulfoxide were then slowly added dropwise at 0° C. The mixture was stirred at 20° C. for a further 4 hours. The reaction mixture was poured into ice-water and extracted with dichloromethane. The organic phase was washed repeatedly with water. Drying of the combined organic phases, removal of the solvent under reduced pressure and chromatography of the residue gave 3.48 g of product (71.4% of theory).

Workup

  1. customdid not exceed 30° C
  2. stirringThe mixture was stirred at 20° C. for a further 4 hours
  3. extractionextracted with dichloromethane
  4. washThe organic phase was washed repeatedly with water
  5. customDrying of the combined organic phases, removal of the solvent under reduced pressure and chromatography of the residue

Sources & evidence

ORD record
ord-6ab0ab22417549c3b1cf3268a2847b8b
Source dataset
uspto-grants-2012_10
Patent number
US08298994B2

Reaction notes

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