Imidazole → HCID 12786191, compound

HRID 126731Notes

Reaction equation

HRID 126731 reaction equation
[OH:1][C:2]([CH2:10][O:11][Si:12]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:13][CH3:14])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5].N1C=CN=C1.Cl[Si:25]([CH3:28])([CH3:27])[CH3:26]>CN(C)C=O>[CH2:13]([Si:12]([CH2:17][CH3:18])([CH2:15][CH3:16])[O:11][CH2:10][C:2]([O:1][Si:25]([CH3:28])([CH3:27])[CH3:26])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5])[CH3:14]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 20565062HCID 20565062, compound

Product 1

HCID 12786191HCID 12786191, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the 4-hydroxy-4-triethylsilyloxymethyl-1-octyne (prepared in Example 3) and 23.9 g. of imidazole in 50 ml. of dimethylformamide at 0° C., is added with stirring, 21.2 g. of chlorotrimethylsilane. The mixture is stirred for 75 minutes, then poured into ice water and extracted with hexane. The hexane layer is washed with water, then saturated sodium bicarbonate solution, dried over magnesium sulfate and the hexane is removed. The residue is distilled. The fraction boiling at 133°-136° C. (1.2 mm.) is collected giving the desired product as a colorless liquid.

Workup

  1. stirringThe mixture is stirred for 75 minutes
  2. extractionextracted with hexane
  3. washThe hexane layer is washed with water
  4. dry with materialsaturated sodium bicarbonate solution, dried over magnesium sulfate
  5. customthe hexane is removed
  6. distillationThe residue is distilled
  7. customThe fraction boiling at 133°-136° C. (1.2 mm.) is collected

Sources & evidence

ORD record
ord-5a96b77a83184bbb8b611c272414901c
Source dataset
uspto-grants-1981_03
Patent number
US04254036

Reaction notes

Loading…