Water → HCID 57541857, compound

HRID 2422233Notes

Reaction equation

HRID 2422233 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[Na+].Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:23][CH:22]=2)=[CH:15][CH:14]=1.O>CN(C)C=O>[CH3:1][N:2]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:23][CH:22]=2)=[CH:17][CH:18]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7515N-MethylanilineHCID 24758Sodium hydrideHCID 67145968HCID 67145968, compound

Product 1

HCID 57541857HCID 57541857, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Methylaniline (57 mg, 0.53 mmol) was dissolved in N,N-dimethylformamide (5 mL), and 60% sodium hydride (21 mg, 0.53 mmol) was added under ice-cooling. The reaction mixture was stirred for 30 min., and methyl 4-[[4-(bromomethyl) phenyl]methoxy]benzenepropanoate (0.15 g, 0.41 mmol) was added. The mixture was stirred at room temperature for 3 hrs, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=18:1) to give the title compound (74 mg, yield 45%) as a yellow powder.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 3 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=18:1)

Sources & evidence

ORD record
ord-d432836bbd214735931ff23e558b22e6
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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