Imidazole → HCID 14330162, compound

HRID 477400Notes

Reaction equation

HRID 477400 reaction equation
[C:1]([C:5]1([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[CH2:7][O:6]1)([CH3:4])([CH3:3])[CH3:2].[NH:16]1[CH:20]=[CH:19][N:18]=[CH:17]1>C(#N)C.C(OCC)(=O)C>[C:1]([C:5]([OH:6])([CH2:7][N:16]1[CH:20]=[CH:19][N:18]=[CH:17]1)[CH2:8][O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 795ImidazoleHCID 19835580HCID 19835580, compound

Product 1

HCID 14330162HCID 14330162, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 59 g (0.28 mol of 2-tert.-butyl-2-(tetrahydro-2H-pyran-2-yloxy-methyl)-oxirane in 100 ml of acetonitrile is added dropwise to a mixture of 119 g 1.75 mol of imidazole, 1 g 9 mols) of potassium tert.-butylate and 500 ml of acetonitrile under a nitrogen atmosphere, the reaction mixture being boiled under reflux. When the addition has ended, the mixture is boiled under reflux for a further 10 hours, the solvent is then stripped off under reduced pressure and the residue which remains is taken up in ethyl acetate. The organic phase is washed with water, dried over sodium sulphate and concentrated under reduced pressure. The product thus obtained is purified chromatographically over silica gel with chloroform as the mobile phase. 56.3 g (72% of theory) of 2-tert.-butyl-3-(imidazol-1-yl)-1-(tetrahydro-2H-pyran-2-yloxy)-propan-2-ol are obtained in this manner in the form of a solid substance of melting point 107° C.

Workup

  1. temperatureunder reflux
  2. additionWhen the addition
  3. temperatureunder reflux for a further 10 hours
  4. washThe organic phase is washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe product thus obtained
  8. customis purified chromatographically over silica gel with chloroform as the mobile phase

Sources & evidence

ORD record
ord-9252648528084ff7ae99bbb57da6248f
Source dataset
uspto-grants-1989_12
Patent number
US04888048

Reaction notes

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