Imidazole → Trimethyl[(oct-1-yn-4-yl)oxy]silane

HRID 460929Notes

Reaction equation

HRID 460929 reaction equation
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5].N1C=CN=C1.Cl[Si:16]([CH3:19])([CH3:18])[CH3:17]>CN(C)C=O>[CH3:17][Si:16]([CH3:19])([CH3:18])[O:1][CH:2]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 1036561-Octyn-4-ol

Product 1

HCID 12786181Trimethyl[(oct-1-yn-4-yl)oxy]silane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cold solution of 166 g of 4-hydroxy-1-octyne [Prostaglandins, 10, 289 (1975)], and 240 g of imidazole in one liter of dimethylformamide is added dropwise 202 g of chlorotrimethylsilane. The mixture is allowed to stand at room temperature for 2 to 3 days. The mixture is partitioned with water and hexane. The hexane layer is washed with brine, dried over magnesium sulfate, and concentrated. Distillation of the residue gives a colorless liquid, b.p. 38° (0.2mm).

Workup

  1. customThe mixture is partitioned with water and hexane
  2. washThe hexane layer is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. distillationDistillation of the residue
  6. customgives a colorless liquid, b.p. 38° (0.2mm)

Sources & evidence

ORD record
ord-b178432bfd8b4ffc9966f14c1d911eda
Source dataset
uspto-grants-1977_12
Patent number
US04061670

Reaction notes

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