Water → HCID 22320094, compound

HRID 1108609Notes

Reaction equation

HRID 1108609 reaction equation
[OH:1][CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1.[H-].[Na+].[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24]Cl.O>CN(C)C=O>[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][O:1][CH:2]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:3]1[CH:4]=[CH:5][C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 11776502HCID 11776502, compound

Product 1

HCID 22320094HCID 22320094, compoundYield 8.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.66 g (19.23 mmol) of methyl α-hydroxy-α-phenyl-p-toluate was dissolved in 50 ml of N,N-dimethylformamide. 0.77 g (19.23 mmol) of 60% sodium hydride was added thereto and the mixture was stirred at room temperature for 1 hour. 3.10 g (28.85 mmol) of 2-dimethylaminoethyl chloride was added thereto and the mixture was heated at 80° C. for 2.5 hours. After the reaction mixture was cooled and poured into water, the obtained mixture was extracted twice with ethyl acetate and the extract was washed with brine, and dried (MgSO4). The solvent was distilled off and the resulting residue was purified by silica gel column chromatography (chloroform:methanol=40:1 (v/v)) to obtain 0.53 g (1.69 mmol) of methyl α-(2-dimethylaminoethoxy)-α-phenyl-p-toluate as a brown oily substance. Its spectroscopic data are as follows:

Workup

  1. temperaturethe mixture was heated at 80° C. for 2.5 hours
  2. temperatureAfter the reaction mixture was cooled
  3. extractionthe obtained mixture was extracted twice with ethyl acetate
  4. washthe extract was washed with brine
  5. dry with materialdried (MgSO4)
  6. distillationThe solvent was distilled off
  7. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol=40:1 (v/v))

Sources & evidence

ORD record
ord-b86a854059714d3aad305d9c4c1fa763
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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