Ethyl cyanoacetate → HCID 54413059, compound

HRID 1704729

Reaction equation

HRID 1704729 reaction equation
CC[O-].[Na+].[C:5]([CH2:7][C:8](OCC)=[O:9])#[N:6].[C:13]1([CH:19]=[C:20]2[C:25](=[O:26])[C:24](=[CH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:23][S:22][CH2:21]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CCO>[O:9]=[C:8]1[O:26][C:25]2[C:24](=[CH:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:23][S:22][CH2:21][C:20]=2[CH:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:7]1[C:5]#[N:6]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 336779tetrahydro-3,5-bis(phenylmethylene)-4H-thiopyran-4-oneHCID 2723922Sodium ethoxide

Product 1

HCID 54413059HCID 54413059, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of NaOEt (from 555 mg, 92 mg atom Na in absolute EtOH) in 100 ml of absolute EtOH is added ethyl cyanoacetate (2.44 g, 22 mmole) dissolved in 50 ml of absolute EtOH. This is heated at reflux temperature for 2 hours, cooled slightly and tetrahydro-3,5-bis(phenylmethylene)-4H-thiopyran-4-one (5.84 g, 20 mmole) is added at once. The mixture quickly turns orange-red for ca. 10 minutes, changing to yellow (yellow solids in orange-red solution) as heating is continued for 2 hours.

Workup

  1. temperatureThis is heated
  2. temperatureat reflux temperature for 2 hours
  3. temperaturecooled slightly
  4. temperatureas heating
  5. waitis continued for 2 hours

Sources & evidence

ORD record
ord-b0cd7425e0bf47af9e85693cd6ceaf55
Source dataset
uspto-grants-1978_11
Patent number
US04127667

Linked notes

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