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

HRID 2164383Notes

Reaction equation

HRID 2164383 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° (0.2 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-eca7991227ed418b85f205f8a264a379
Source dataset
uspto-grants-1985_03
Patent number
US04504417

Reaction notes

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