Sodium hydride → HCID 24782634, compound

HRID 1685803Notes

Reaction equation

HRID 1685803 reaction equation
[C:1]([CH:3]1[CH2:7][S:6][CH2:5][C:4]1=[O:8])#[N:2].[H-].[Na+].Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:15][CH:14]=1>CN(C)C=O>[C:1]([C:3]1([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([CH:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:17][CH:18]=2)[C:4](=[O:8])[CH2:5][S:6][CH2:7]1)#[N:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3266764-Cyano-3-tetrahydrothiophenoneHCID 11242311Loxoprofen Impurity 18

Product 1

HCID 24782634HCID 24782634, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Cyano-3-tetrahydrothiophenone (5.0 g) was dissolved in N,N-dimethylformamide (30 ml), then, sodium hydride (oil, about 60%, 950 mg) was added under ice cooling, and stirred at the same temperature for 30 minutes. Then, to the mixture was added a solution of methyl 2-(4-bromomethylphenyl)propionate (10.1 g) in N,N-dimethylformamide (10.0 ml) under ice cooling, and the reaction mixture was stirred overnight at room temperature. The reaction mixture was quenched with water, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give the title compound (5.5 g, 46%).

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-97b31bd10c3d41a797fdba994730c520
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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