Butanal → Methyl 3-ethyl-6-(propan-2-yl)azulene-1-carboxylate

HRID 1165890Notes

Reaction equation

HRID 1165890 reaction equation
[CH:1](=O)[CH2:2][CH2:3]C.N1CCOCC1.[CH3:12][O:13][C:14]([C:16]1[C:20](=O)O[C:18]2=[CH:22][CH:23]=[C:24]([CH:27]([CH3:29])[CH3:28])[CH:25]=[CH:26][C:17]=12)=[O:15]>C(O)C>[CH3:12][O:13][C:14]([C:16]1[C:17]2[C:18]([CH:22]=[CH:23][C:24]([CH:27]([CH3:29])[CH3:28])=[CH:25][CH:26]=2)=[C:1]([CH2:2][CH3:3])[CH:20]=1)=[O:15]

Participants

5

Reactant 3

HCID 261ButanalHCID 8083MorpholineHCID 14515736HCID 14515736, compound

Product 1

HCID 14515737Methyl 3-ethyl-6-(propan-2-yl)azulene-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

n-Butyraldehyde (61.5 g, 0.853 mole) and morpholine (61.9 g, 0.71 mole) are added to cooled ethanol (400 ml), and then the compound (5) (68 g, 0.276 mole) is added thereto. The obtained mixture is stirred and warmed to dissolve the solid substance homogeneously. It is heated under reflux for 8 hours, and then the solvent is distilled off under reduced pressure to precipitate an oily material. The obtained oily material is dissolved in benzene (450 ml), washed twice with the same volume of water, three times with 1N HCl (400 ml), and further twice with water (400 ml). The obtained benzene solution is passed through alumina (500 g), and the eluted solution is concentrated to obtain the compound (1) at a yield of 57.4 g, 81.2%. It is recrystallized in n-hexane to give the purified product (55 g) in the purple crystalline form.

Workup

  1. temperaturewarmed
  2. dissolutionto dissolve the solid substance homogeneously
  3. temperatureIt is heated
  4. temperatureunder reflux for 8 hours
  5. distillationthe solvent is distilled off under reduced pressure
  6. customto precipitate an oily material
  7. dissolutionThe obtained oily material is dissolved in benzene (450 ml)
  8. washwashed twice with the same volume of water, three times with 1N HCl (400 ml)
  9. concentrationthe eluted solution is concentrated

Sources & evidence

ORD record
ord-0729a19b91db4056a76c1689346056a7
Source dataset
uspto-grants-1990_03
Patent number
US04912134

Reaction notes

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