Water → HCID 14769750, compound

HRID 1090348Notes

Reaction equation

HRID 1090348 reaction equation
[C:1]([C:5]1([CH:8]2[CH2:12][O:11][C:10]([CH3:14])([CH3:13])[O:9]2)[CH2:7][O:6]1)([CH3:4])([CH3:3])[CH3:2].N1C=[CH:18][N:17]=[N:16]1.[OH-].[Na+].O.[CH3:23][N:24](C)C=O>>[CH3:2][C:1]([CH3:4])([CH3:3])[C:5]([CH:8]1[CH2:12][O:11][C:10]([CH3:14])([CH3:13])[O:9]1)([CH2:7][N:17]1[CH:18]=[N:24][CH:23]=[N:16]1)[OH:6]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 14675583HCID 14675583, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 14769750HCID 14769750, compoundYield 26%

Conditions

Temperature
100 °C

Procedure

12.4 g (0.062 mol) of 2-t-butyl-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-oxirane, 5.1 g (0.074 mol) of triazole and 3 g (0.074 mol) of sodium hydroxide are dissolved in 60 ml of dimethylformamide and the mixture is stirred at 100° C. for 10 hours. For working up, the cooled reaction mixture is introduced into water and extracted with ethyl acetate, the organic phase is washed with water, dried over sodium sulphate and concentrated in vacuo and the residue is purified by column chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 3:1). 4.4 g (26% of theory) of 2,2-dimethyl-1-(2,2-dimethyl-1,3-dioxolan-4-yl)-1-(1,2,4-triazol-1-yl-methyl)-propan-1-ol are obtained as an oil of refractive index nD20 1.4890;

Workup

  1. customthe cooled reaction mixture
  2. extractionextracted with ethyl acetate
  3. washthe organic phase is washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customthe residue is purified by column chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 3:1)

Sources & evidence

ORD record
ord-6a0f449d282841cabc540d16c09d31e7
Source dataset
uspto-grants-1992_01
Patent number
US05081265

Reaction notes

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