Ethanol → Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate

HRID 1634634Notes

Reaction equation

HRID 1634634 reaction equation
[BH4-].[Na+].C(O)C.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[CH:20][N:21]([CH3:23])[CH3:22])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][CH:9]=1>O>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]([CH2:20][N:21]([CH3:23])[CH3:22])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 69859264HCID 69859264, compound

Product 1

HCID 11345737Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionateYield 21%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A gentle nitrogen flow was applied to a 100 ml balloon flask provided with magnetic stirring and 0.455 g (0.0120 mol) of sodium borohydride was mixed with 10 ml of ethanol. Thereafter, 1 g (0.0040 mol) of ethyl α-(p-methoxyphenyl)-β-(dimethylamino)acrylate was added. The mixture was stirred for 24 hours at room temperature and then 3 ml of water were added. The ethanol was removed in the rotary evaporator and 20 ml of water and 20 ml of dichloromethane were added over the residue. The mixture was stirred and the phases were separated. The process continued with the organic phase. 20 ml of water were added, the mixture was acidified to acid pH and decanted. The aqueous phase was washed with 20 ml of dichloromethane and was then basified to basic pH. The product was extracted from the aqueous phase with 20 ml of dichloromethane. It was dried with sodium sulfate, was filtered and the solvent was removed under vacuum to give 0.21 g of ethyl α-(p-methoxyphenyl)-β-(dimethylamino)propionate (Yield: 21%).

Workup

  1. customA gentle nitrogen flow was applied to a 100 ml balloon flask
  2. customprovided
  3. stirringThe mixture was stirred for 24 hours at room temperature
  4. customThe ethanol was removed in the rotary evaporator and 20 ml of water and 20 ml of dichloromethane
  5. additionwere added over the residue
  6. stirringThe mixture was stirred
  7. customthe phases were separated
  8. addition20 ml of water were added
  9. customdecanted
  10. washThe aqueous phase was washed with 20 ml of dichloromethane
  11. extractionThe product was extracted from the aqueous phase with 20 ml of dichloromethane
  12. dry with materialIt was dried with sodium sulfate
  13. filtrationwas filtered
  14. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-4212286cb5a049a3a18b0235a0ecbbf0
Source dataset
uspto-grants-2003_01
Patent number
US06506941B1

Reaction notes

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