Diethyl (aminomethylidene)propanedioate → HCID 21270447, compound

HRID 1905697Notes

Reaction equation

HRID 1905697 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[NH2:12][CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([NH:12][CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:7][CH2:6]2)[O:4][CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 226751Diethyl (aminomethylidene)propanedioateHCID 521998p-Toluenesulfonic acid monohydrateHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 21270447HCID 21270447, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1,4-Dioxaspiro[4.5]decan-8-one (40 g) and diethyl aminomethylenemalonate (47.94 g) are dissolved in 500 ml of toluene. p-Toluenesulfonic acid monohydrate (2.44 g) and 100 ml of toluene are then added and the mixture is refluxed for 3 days collecting water in a Dean-Stark trap. The resulting mixture is decanted and solvent is removed to leave on oil. This oil is flash chromatographed on 750 g silica gel using 9:1 CH2Cl2, EtOAc as eluant to yield diethyl N-(1,4-dioxaspiro[4.5]decen-8-yl)aminomethylenemalonate as an oil.

Workup

  1. temperaturethe mixture is refluxed for 3 days
  2. customcollecting water in a Dean-Stark trap
  3. customThe resulting mixture is decanted
  4. customsolvent is removed
  5. customto leave on oil
  6. customchromatographed on 750 g silica gel using 9:1 CH2Cl2, EtOAc as eluant

Sources & evidence

ORD record
ord-469b03dce19e46b98cab74032100e854
Source dataset
uspto-grants-1987_03
Patent number
US04647566

Reaction notes

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