Imidazole → 4-Propadienyl-4-trimethylsilyloxy-1-octyne

HRID 848891Notes

Reaction equation

HRID 848891 reaction equation
[OH:1][C:2]([CH:10]=[C:11]=[CH2:12])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5].N1C=CN=C1.CN(C)C=O.Cl[Si:24]([CH3:27])([CH3:26])[CH3:25]>O>[CH:10]([C:2]([O:1][Si:24]([CH3:27])([CH3:26])[CH3:25])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5])=[C:11]=[CH2:12]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 130391884-Hydroxy-4-propadienyl-1-octyne

Product 1

HCID 130391894-Propadienyl-4-trimethylsilyloxy-1-octyne

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred, ice-cold solution of 10.85 g. (66.1 mmol.) of 4-hydroxy-4-propadienyl-1-octyne and 13.2 g. (194 mmol.) of imidazole in 50 ml. of dimethylformamide at 0° C. is added 9.5 ml. of chlorotrimethylsilane. The solution is kept at 0° C. for 70 hours and diluted with petroleum ether. The resulting mixture is shaken with water at 0° C. The organic layer is washed with water and brine, dried over magnesium sulfate and concentrated to give the title compound as a liquid.

Workup

  1. washThe organic layer is washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0b971867760c4dab89b9547cef4ac159
Source dataset
uspto-grants-1981_10
Patent number
US04297516

Reaction notes

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