Acetic Acid → HCID 86702738, compound

HRID 511749Notes

Reaction equation

HRID 511749 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[CH:12]1[C:19](=[O:20])[CH:18]2[CH:14]([CH2:15][C:16](=O)[CH2:17]2)[C:13]1=[O:22])[CH3:2].[C:23](#[N:27])[CH2:24][C:25]#[N:26].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[CH:12]1[C:19](=[O:20])[CH:18]2[CH:14]([CH2:15][C:16](=[C:24]([C:23]#[N:27])[C:25]#[N:26])[CH2:17]2)[C:13]1=[O:22])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8010MalononitrileHCID 517165Ammonium AcetateHCID 67516257HCID 67516257, compound

Product 1

HCID 86702738HCID 86702738, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.500 g (1.70 mmol) of 2-(2,6-diethyl-4-methylphenyl)tetrahydropentalene-1,3,5-trione (example I-a-4 from WO 2010/040460), 250 mg of malononitrile, 150 mg of ammonium acetate and 0.3 ml of glacial acetic acid in 30 ml of toluene are heated at reflux for 2 h. After cooling, the solvent is distilled off and the mixture is taken up in ethyl acetate, washed twice with water, then dried (magnesium sulphate) and concentrated on a rotary evaporator. What remains is a yellow oil which is chromatographed on silica gel using ethyl acetate/hexane 1:6. This gives 0.32 g (56%) of a colourless oil.

Workup

  1. temperatureat reflux for 2 h
  2. temperatureAfter cooling
  3. distillationthe solvent is distilled off
  4. washwashed twice with water
  5. dry with materialdried (magnesium sulphate)
  6. concentrationconcentrated on a rotary evaporator
  7. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-419d9fcfecb44f818a9d889845f24c54
Source dataset
uspto-grants-2015_08
Patent number
US09101133B2

Reaction notes

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