Imidazole → HCID 2760859, compound

HRID 1611741Notes

Reaction equation

HRID 1611741 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][C:4]#[CH:5].N1C=CN=C1.Cl[Si:13]([CH3:16])([CH3:15])[CH3:14]>C(Cl)Cl.O>[CH3:14][Si:13]([CH3:16])([CH3:15])[O:6][CH2:1][CH2:2][CH2:3][C:4]#[CH:5]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 793464-Pentyn-1-ol

Product 1

HCID 2760859HCID 2760859, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-pentyn-1-ol (25.0 g, 0.30 mole) in dry CH2Cl2 (250 ml) at 0° C., was added imidazole (40.46 g, 0.60 mole) and chlorotrimethylsilane (56.6 ml, 0.45 moles) and stirred for 2 h. The reaction mixture was diluted with water and extracted with CH2Cl2 (3×100 ml). Combined organic extracts were washed with water, brine, dried (Na2SO4) and the solvent was evaporated. Purification of the crude product by vacuum distillation afforded the pure ether 13 (44.1 g, 95%).

Workup

  1. extractionextracted with CH2Cl2 (3×100 ml)
  2. washCombined organic extracts were washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent was evaporated
  5. customPurification of the crude product
  6. distillationby vacuum distillation

Sources & evidence

ORD record
ord-ff973ae5ee6f4d6e9e2c05fa05d3a375
Source dataset
uspto-grants-2006_01
Patent number
US06989450B2

Reaction notes

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