Ethyl cyanoacetate → HCID 68025748, compound

HRID 2206302Notes

Reaction equation

HRID 2206302 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([OH:10])=[CH:4][C:3]=2[O:2]1.[CH2:11]([O:14][C:15]1[C:22]([O:23][CH3:24])=[CH:21][C:18]([CH:19]=O)=[CH:17][C:16]=1[Br:25])[CH:12]=[CH2:13].[C:26]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])#[N:27].N1CCCCC1>C(O)C.O>[CH2:32]([O:31][C:29]([C:28]1[CH:19]([C:18]2[CH:21]=[C:22]([O:23][CH3:24])[C:15]([O:14][CH2:11][CH:12]=[CH2:13])=[C:16]([Br:25])[CH:17]=2)[C:6]2[CH:7]=[C:8]3[O:9][CH2:1][O:2][C:3]3=[CH:4][C:5]=2[O:10][C:26]=1[NH2:27])=[O:30])[CH3:33]

Participants

7

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 68289SesamolHCID 21681633-Bromo-5-methoxy-4-(2-propen-1-yloxy)benzaldehyde

Product 1

HCID 68025748HCID 68025748, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

3,4-Methylenedioxyphenol (166 mg, 1.2 mmol), 4-allyloxy-3-bromo-5-methoxy-benzaldehyde (271 g, 1 mmol) and ethyl cyanoacetate (113 mg, 1 mmol) were taken in 7 ml ethanol at room temperature, charged with piperidine (50 μL) and then stirred at 80° C. under LC-MS control till the reaction was complete. The reaction mixture was cooled down to room temperature, diluted with 10 ml water, stirred for 2 h at room temperature, solids were collected by filtration, washed with 1:1 mixture of ethanol/water and dried (239 mg, 0.47 mmol, 47%).

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. stirringstirred for 2 h at room temperature
  3. filtrationsolids were collected by filtration
  4. washwashed with 1:1 mixture of ethanol/water
  5. customdried (239 mg, 0.47 mmol, 47%)

Sources & evidence

ORD record
ord-081b9fb5cbe147a99c42b073140ca8f3
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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