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

HRID 1413572Notes

Reaction equation

HRID 1413572 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 grams of 4-hydroxy-1-octyne [Prostaglandins, 10, 289 (1975)], and 240 grams of imidazole in one liter of dimethylformamide is added dropwise 202 grams of chlorotrimethylsilane. The mixture is allowed to stand at room temperature for about 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° (0.2 mm).

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° (0.2 mm)

Sources & evidence

ORD record
ord-8d0e53e87af3466290c67f376277e1f4
Source dataset
uspto-grants-1981_02
Patent number
US04250325

Reaction notes

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