Sodium → HCID 18783964, compound

HRID 1108612Notes

Reaction equation

HRID 1108612 reaction equation
[CH3:1][N:2]([CH3:25])[CH2:3][CH2:4][O:5][CH:6]([C:13]1[CH:24]=[CH:23][C:16]([CH:17]=[CH:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Na]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:25][N:2]([CH3:1])[CH2:3][CH2:4][O:5][CH:6]([C:13]1[CH:24]=[CH:23][C:16]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 5360545SodiumHCID 54228423HCID 54228423, compound

Product 1

HCID 18783964HCID 18783964, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

0.19 g (0.560 mmol) of methyl 4-[α-(2-dimethylaminoethoxy)benzyl]cinnamate was dissolved in 4 ml of methanol and 13 mg (0.056 mmol) of nickel chloride hexahydrate was then added. Forty-two mg (1.12 mmol) of sodium boronhydride was further added thereto under ice-cooling in divided portions for 1 hour and stirred for further 45 minutes. The reaction mixture was filtered and the filtrate was concentrated. The resulting residue was dissolved in chloroform and washed with water and brine. After the organic phase was dried (MgSO4), the solvent was distilled off and the residue was purified by silica gel column chromatography (chloroform:methanol=50:1 (v/v)) to obtain 0.10 g (0.293 mmol) of methyl 3-{4-[α-(2-dimethylaminoethoxy)benzyl]phenyl}propionate as a colorless oily substance. Its spectroscopic data are as follows:

Workup

  1. temperatureunder ice-cooling in divided portions for 1 hour
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe resulting residue was dissolved in chloroform
  5. washwashed with water and brine
  6. dry with materialAfter the organic phase was dried (MgSO4)
  7. distillationthe solvent was distilled off
  8. customthe residue was purified by silica gel column chromatography (chloroform:methanol=50:1 (v/v))

Sources & evidence

ORD record
ord-5ef7f0f561554b168090bf50d7b1b31b
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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