Imidazole → 4-Trimethylsilylethynyl-1-octyn-4-ol trimethylsilyl ether

HRID 1413571Notes

Reaction equation

HRID 1413571 reaction equation
[CH3:1][Si:2]([C:5]#[C:6][C:7]([OH:15])([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:8][C:9]#[CH:10])([CH3:4])[CH3:3].N1C=CN=C1.Cl[Si:22]([CH3:25])([CH3:24])[CH3:23].CCCCCC>CN(C)C=O>[CH3:23][Si:22]([O:15][C:7]([C:6]#[C:5][Si:2]([CH3:3])([CH3:1])[CH3:4])([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:8][C:9]#[CH:10])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 8058HexaneHCID 127861934-Trimethylsilylethynyl-1-octyn-4-ol

Product 1

HCID 572330774-Trimethylsilylethynyl-1-octyn-4-ol trimethylsilyl ether

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 8.5 grams of 4-trimethylsilylethynyl-1-octyn-4-ol and 6.2 grams of imidazole in 24 ml of dry dimethylformamide is added, under nitrogen, 5.7 ml of chlorotrimethylsilane, in a slow stream, via a syringe. The mixture is stirred in an ice bath for one hour and then at room temperature overnight. The mixture is poured into hexane, washed with saturated sodium bicarbonate solution, water and then brine and dried over sodium sulfate. The solvents are evaporated to dryness yielding 11.1 grams of the desired product.

Workup

  1. additionis added, under nitrogen
  2. customat room temperature
  3. customovernight
  4. washwashed with saturated sodium bicarbonate solution, water
  5. dry with materialbrine and dried over sodium sulfate
  6. customThe solvents are evaporated to dryness

Sources & evidence

ORD record
ord-f4c1688de1684c598f18be5b84cd3764
Source dataset
uspto-grants-1981_02
Patent number
US04250325

Reaction notes

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