Imidazole → 7-Chloro-4-methyl-4-trimethylsilyloxy-1-heptyne

HRID 1065169Notes

Reaction equation

HRID 1065169 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([OH:10])([CH3:9])[CH2:6][C:7]#[CH:8].CN(C)C=O.N1C=CN=C1.Cl[Si:22]([CH3:25])([CH3:24])[CH3:23]>O>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([CH3:9])([O:10][Si:22]([CH3:25])([CH3:24])[CH3:23])[CH2:6][C:7]#[CH:8]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 128987397-Chloro-4-hydroxy-4-methyl-1-heptyne

Product 1

HCID 128987407-Chloro-4-methyl-4-trimethylsilyloxy-1-heptyne

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 7-chloro-4-hydroxy-4-methyl-1-heptyne in 80 ml. of dimethylformamide at 0° C., is added 43.8 g. (0.644 moles) of imidazole and 35.02 g. (0.322 moles) of chlorotrimethylsilane. The mixture is stirred at room temperature for 45 minutes, poured into water and extracted with hexane. The hexane solution is washed with dilute sodium bicarbonate solution, dried over magnesium sulfate and the solvent removed leaving an orange liquid. This liquid is distilled giving the desired product in the fraction boiling at 83°-88° C., 1.5 mm. as a colorless liquid.

Workup

  1. extractionextracted with hexane
  2. washThe hexane solution is washed with dilute sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent removed
  5. customleaving an orange liquid
  6. distillationThis liquid is distilled

Sources & evidence

ORD record
ord-2ea2d71201ae4f85a20b0b7b6d0a2835
Source dataset
uspto-grants-1982_05
Patent number
US04328359

Reaction notes

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