Acetic Acid → HCID 68717432, compound

HRID 1947246Notes

Reaction equation

HRID 1947246 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][CH3:12])=O.[O:13]=[C:14]([CH3:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(O)(=O)C.N1CCCCC1>ClCCl>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH:1]=[C:15]([C:14](=[O:13])[CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:4]([O:11][CH3:12])[CH:5]=1)#[N:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 8868Ethyl AcetoacetateHCID 166592514-Formyl-3-methoxybenzonitrile

Product 1

HCID 68717432HCID 68717432, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3 g (18.61 mmol) of 4-formyl-3-methoxybenzonitrile, 2.6 ml (20.47 mmol) of ethyl 3-oxobutanoate, 1.33 ml (23.26 mmol) of acetic acid and 0.18 ml (1.85 mmol) of piperidine are stirred in 70 ml of dry dichloromethane under reflux with a water trap for 24 h. After cooling, the reaction solution is washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated. The residue is recrystallized from diethyl ether. 5.01 g (98% of theory) of the title compound are obtained as E/Z isomer mixture in the form of a pale yellow solid.

Workup

  1. temperatureunder reflux with a water trap for 24 h
  2. temperatureAfter cooling
  3. washthe reaction solution is washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is recrystallized from diethyl ether

Sources & evidence

ORD record
ord-5e3179b77d3c4d4e84178d5b416928b5
Source dataset
uspto-grants-2013_03
Patent number
US08399471B2

Reaction notes

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