Imidazole → HCID 86099274, compound

HRID 708536Notes

Reaction equation

HRID 708536 reaction equation
N1C=CN=C1.[C:6]([Si:10](Cl)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:9])([CH3:8])[CH3:7].[Cl:24][CH2:25][C:26]#[C:27][CH2:28][OH:29]>C(Cl)Cl.C(Cl)Cl.O>[C:6]([Si:10]([O:29][CH2:28][C:27]#[C:26][CH2:25][Cl:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 2027752-Butyn-1-ol, 4-chloro-

Product 1

HCID 86099274HCID 86099274, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21908982Water methylene chlorideSolvent

Procedure

To a solution of imidazole (691 mg, 10.2 mmol) and tert-butylchlorodiphenylsilane (2.65 ml, 10.1 mmol) in DCM (15.3 mL) at 0° C. was added 4-chlorobut-2-yn-1-ol (824 μL, 9.18 mmol). After 2 h of stirring at rt it was diluted with DCM/water and the layers were separated. The aqueous layer was extracted with DCM (2×) and the combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude residue dissolved in dioxane and reconcentrated (2×) then used directly without further purification.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with DCM (2×)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude residue dissolved in dioxane
  7. customthen used directly without further purification

Sources & evidence

ORD record
ord-d7011d5e345b45b2ab745083b1cb59d2
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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