Diethyl (ethoxymethylene)malonate → HCID 59718769, compound

HRID 383529Notes

Reaction equation

HRID 383529 reaction equation
[CH3:1][CH2:2][C:3](=O)[CH2:4][CH3:5].[CH2:7]([NH2:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(O[CH:18]=[C:19]([C:25]([O:27]CC)=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21])C>C1(C)C=CC=CC=1>[CH2:7]([N:14]1[C:3]([CH2:4][CH3:5])=[C:2]([CH3:1])[CH:18]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:25]1=[O:27])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 7288Ethyl ketoneHCID 7504Benzylamine

Product 1

HCID 59718769HCID 59718769, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A toluene solution (50 mL) of 3-pentanone (5.00 g, 58.1 mmol) and benzylamine (6.23 g, 58.1 mmol) was heated and refluxed under azeotropic dehydration for 3 hours. After that, diethyl ethoxymethylenemalonate (12.56 g, 58.1 mmol) was added, and the mixture was further continued to be heated and refluxed for 5 hours. The solvent was removed by distillation under reduced pressure, and the residue was refined with silica gel (300 g) column chromatography (ethyl acetate-hexane of 1:5 in mixing ratio and then those of 1:3 and 2:1), and pale yellow oily matter (AA06, 1.92 g, 11.0%) was obtained.

Workup

  1. temperaturerefluxed under azeotropic dehydration for 3 hours
  2. temperatureto be heated
  3. temperaturerefluxed for 5 hours
  4. customThe solvent was removed by distillation under reduced pressure
  5. additionin mixing ratio
  6. customthose of 1:3 and 2:1), and pale yellow oily matter (AA06, 1.92 g, 11.0%) was obtained

Sources & evidence

ORD record
ord-5d1950b1ee7c44849089187cfb5cab71
Source dataset
uspto-grants-2013_02
Patent number
US08367666B2

Reaction notes

Loading…