Ethyl cyanoacetate → HCID 178440245, compound

HRID 531144Notes

Reaction equation

HRID 531144 reaction equation
O=C(CCC)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].CO[CH:14]([O:18]C)[N:15]([CH3:17])C.[C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])#N.C(N(C(C)C)[CH:31]([CH3:33])[CH3:32])C>C(O)C.O.C(O)(=O)C>[OH:18][C:14]1[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:20][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:17]([CH2:32][CH2:31][CH3:33])[N:15]=1

Participants

8

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 78373Dimethylformamide dimethyl acetalHCID 81531DiisopropylethylamineHCID 238498Ethyl 3-oxohexanoate

Product 1

HCID 178440245HCID 178440245, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolvent3×HCID 962WaterSolvent2×

Conditions

Temperature
45 °C

Procedure

A mixture of ethyl 3-oxohexanoate (20.0 g) and 1,1-dimethoxy-N,N-dimethylmethanamine (15.8 g) in ethanol (40 mL) was stirred at 40 to 50° C. for 3 hours. After cooling to 25° C., ethyl cyanoacetate (15.7 g) was added to the mixture followed by addition of N-ethyl-N-isopropylpropan-2-amine (22.1 mL) at room temperature. The mixture was stirred at 50° C. for 16 hours. Acetic acid (9.11 g) and ethanol (40 mL) were added to the mixture at room temperature. The mixture was warmed to 50° C., and water (100 mL) was charged. The suspension was cooled to room temperature and stirred for 30 minutes. The precipitate was collected by filtration, washed with ethanol-water (20 mL-80 mL) and dried at 70° C. under vacuum to give a white solid. This solid was dissolved in ethanol (200 mL) at reflux temperature. Water (150 mL) was added to the mixture at the same temperature. The mixture was cooled gradually, stirred at 50 to 60° C. for 1 hour and at room temperature for 2 hours. The precipitate was collected by filtration, washed with ethanol-water (25 mL-25 mL) and dried at 70° C. under vacuum to give the title compound (17.5 g).

Workup

  1. temperatureAfter cooling to 25° C.
  2. stirringThe mixture was stirred at 50° C. for 16 hours
  3. temperatureThe mixture was warmed to 50° C.
  4. temperatureThe suspension was cooled to room temperature
  5. stirringstirred for 30 minutes
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with ethanol-water (20 mL-80 mL)
  8. customdried at 70° C. under vacuum
  9. customto give a white solid
  10. temperatureat reflux temperature
  11. temperatureThe mixture was cooled gradually
  12. stirringstirred at 50 to 60° C. for 1 hour and at room temperature for 2 hours
  13. filtrationThe precipitate was collected by filtration
  14. washwashed with ethanol-water (25 mL-25 mL)
  15. customdried at 70° C. under vacuum

Sources & evidence

ORD record
ord-72201acdc1cb4a648e80bf59d3b016cd
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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