Water → HCID 54228423, compound

HRID 1108611Notes

Reaction equation

HRID 1108611 reaction equation
[OH:1][CH:2]([C:9]1[CH:20]=[CH:19][C:12]([CH:13]=[CH:14][C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[Na+].[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26]Cl.O>CN(C)C=O>[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][O:1][CH:2]([C:9]1[CH:10]=[CH:11][C:12]([CH:13]=[CH:14][C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 54294312HCID 54294312, compound

Product 1

HCID 54228423HCID 54228423, compoundYield 4.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.04 g (11.33 mmol) of methyl 4-(α-hydroxybenzyl)cinnamate was dissolved in 35 ml of N,N-dimethylformamide, thereafter 0.45 g (11.33 mmol) of 60% sodium hydride was added thereto, and the mixture was stirred overnight at room temperature. 2.44 g (22.66 mmol) of 2-dimethylaminoethyl chloride was then added thereto. The resulting mixture was heated at 80° C. and stirred for 5 hours. After cooling, the reaction mixture was poured into water, the obtained mixture was extracted twice with ethyl acetate, and the extract was washed with brine. The organic phase was dried (MgSO4) and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography (chloroform:methanol =50:1 (v/v)) followed by alumina column chromatography (n-hexane:ethyl acetate=5:1 (v/v)) to obtain 0.19 g (0.560 mmol) of methyl 4-[α-(2-dimethylaminoethoxy)benzyl]cinnamate as a pale yellow oily substance. Its spectroscopic data are as follows:

Workup

  1. temperatureThe resulting mixture was heated at 80° C.
  2. stirringstirred for 5 hours
  3. temperatureAfter cooling
  4. extractionthe obtained mixture was extracted twice with ethyl acetate
  5. washthe extract was washed with brine
  6. dry with materialThe organic phase was dried (MgSO4)
  7. distillationthe solvent was distilled off
  8. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol =50:1 (v/v))

Sources & evidence

ORD record
ord-d03db51a159a42b89bce4e292a2174b5
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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