Aluminum → HCID 53942418, compound

HRID 568750Notes

Reaction equation

HRID 568750 reaction equation
[Cl:1][CH2:2][C:3]([CH3:21])([CH3:20])[C:4](=[O:19])[C:5]([N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[Al]>C(O)(C)C>[Cl:1][CH2:2][C:3]([CH3:21])([CH3:20])[C:4](=[O:19])[C:5]([N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)=[CH:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1.[Cl:1][CH2:2][C:3]([CH3:21])([CH3:20])[C:4]([OH:19])=[C:5]([N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 5359268AluminumHCID 53942418HCID 53942418, compound

Product 2

HCID 53942418HCID 53942418, compoundHCID 70372778HCID 70372778, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

48.6 g (0.15 mole) of 1-chloro-5-(4-chlorophenyl)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-4-penten-3-one (prepared as described in Example 1) and 30.6 g (0.15 mole) of aluminium isopropylate in 200 ml of isopropanol were heated under reflux for 7 hours, isopropanol and acetone being continuously distilled off over a 30 cm Vigreux column until acetone could no longer be detected in the distillate. The reaction mixture was then concentrated and ice/hydrochloric acid was added to the residue. The mixture was extracted with methylene chloride. The combined methylene chloride extracts were dried over sodium sulphate and concentrated in vacuo. The oily residue was subjected to separation by column chromatography (silica gel/chloroform). The non-reduced E-isomer of 1-chloro-5-(4-chlorophenyl)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-penten-3-one (the compound of Example 2) and pure 1-chloro-5-(4-chlorophenyl)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-penten-3-ol of melting point 120° C., as the Z-isomer, were obtained.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 7 hours
  3. distillationisopropanol and acetone being continuously distilled off over a 30 cm Vigreux column until acetone
  4. concentrationThe reaction mixture was then concentrated
  5. additionice/hydrochloric acid was added to the residue
  6. extractionThe mixture was extracted with methylene chloride
  7. dry with materialThe combined methylene chloride extracts were dried over sodium sulphate
  8. concentrationconcentrated in vacuo
  9. customThe oily residue was subjected to separation by column chromatography (silica gel/chloroform)

Sources & evidence

ORD record
ord-8b139e683e9e40adbc234528c9c5eb5b
Source dataset
uspto-grants-1988_03
Patent number
US04729783

Reaction notes

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