Aluminum isopropoxide → HCID 19822124, compound

HRID 1030252Notes

Reaction equation

HRID 1030252 reaction equation
[CH:1]([CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1([C:16](=[N:27][CH3:28])[S:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:2].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-]>C(O)(C)C>[OH:2][CH2:1][CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1([C:16](=[N:27][CH3:28])[S:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 11143Aluminum isopropoxideHCID 19822113HCID 19822113, compound

Product 1

HCID 19822124HCID 19822124, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2-formylmethyl-1-((N-methylimino)-(4-methoxybenzylthio)methyl)-1-(pyrid-3-yl)cyclohexane (1 g, 2.52 mmol) and aluminium isopropoxide (1.03 g, 5.04 mmol) in dry isopropanol (50 ml) were heated at reflux under a McIntyre head under argon for 5 hr. After cooling, the solution was concentrated in vacuo and the residue treated with dichloromethane (50 ml) and Rochelle salt solution (20 ml). The layers were filtered and separated, and the organic layer washed with water, dried (MgSO4) and concentrated in vacuo to give a cream solid. Recrystallisation from ethyl acetate gave 2-(2-hydroxyethyl)-1-((N-methylimino)-(4-methoxybenzylthio)methyl)-1-(pyrid-3-yl)cyclohexane (0.5 g) as a white solid, m.p. 145°-146° C.;

Workup

  1. temperaturewere heated
  2. temperatureat reflux under a McIntyre head under argon for 5 hr
  3. temperatureAfter cooling
  4. concentrationthe solution was concentrated in vacuo
  5. additionthe residue treated with dichloromethane (50 ml) and Rochelle salt solution (20 ml)
  6. filtrationThe layers were filtered
  7. customseparated
  8. washthe organic layer washed with water
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo
  11. customto give a cream solid
  12. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-be2cfbac64ec43b98ee08bcbeb133ba2
Source dataset
uspto-grants-1992_04
Patent number
US05104883

Reaction notes

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