Hydrochloric Acid → Triapenthenol

HRID 1709738Notes

Reaction equation

HRID 1709738 reaction equation
[CH:1]1([CH:7]=[C:8]([N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>O1CCCC1>[CH:1]1(/[CH:7]=[C:8](/[N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)\[CH:9]([OH:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 566097071-Cyclohexyl-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one

Product 1

HCID 6437842Triapenthenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

29 ml (0.029 mol) of boron hydride-tetrahydrofuran complex are added to a solution of 4.1 g (0.0145 mol) of S-2-(dibenzyl-hydroxymethyl)-pyrrolidine in 30 ml of absolute tetrahydrofuran at 20° C., with stirring. After the mixture has been stirred at 20° C. for 30 minutes, 2.61 g (0.01 mol) of the (E)-isomer of 1-cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-en-3-one are added and the mixture is stirred at 40° C. for a further 16 hours. Thereafter, the reaction mixture is poured into 100 ml of 2N aqueous hydrochloric acid. The mixture formed is extracted twice with methylene chloride and the combined organic phases are concentrated under reduced pressure. The residue which remains is chromatographed with a mixture of chloroform/ethyl acetate=4:1 on silica gel. 2.3 g (87% of theory) of the (-)-antipode of (E)-1-cyclohexyl-4,4-dimethyl-3-hydroxy-2-(1,2,4-triazol-1-yl)-pent-1-ene are obtained in this manner in the form of a crystalline product.

Workup

  1. stirringAfter the mixture has been stirred at 20° C. for 30 minutes
  2. stirringthe mixture is stirred at 40° C. for a further 16 hours
  3. customThe mixture formed
  4. extractionis extracted twice with methylene chloride
  5. concentrationthe combined organic phases are concentrated under reduced pressure
  6. customThe residue which remains is chromatographed with a mixture of chloroform/ethyl acetate=4:1 on silica gel

Sources & evidence

ORD record
ord-9d1e0e844a2d4517a23e26f2c971be98
Source dataset
uspto-grants-1990_08
Patent number
US04950767

Reaction notes

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