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

HRID 1395172Notes

Reaction equation

HRID 1395172 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 2to 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, bp 38° C. (0.2 mm).

Workup

  1. customto stand at room temperature for 2to 3 days
  2. customThe mixture is partitioned with water and hexane
  3. washThe hexane layer is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. distillationDistillation of the residue
  7. customgives a colorless liquid, bp 38° C. (0.2 mm)

Sources & evidence

ORD record
ord-fda07c43662242e2bee3df36d5711b19
Source dataset
uspto-grants-1980_05
Patent number
US04202822

Reaction notes

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