Imidazole → (+/-) 4-Trimethylsilyloxy-4-n-propyl-1-octyne

HRID 1106292Notes

Reaction equation

HRID 1106292 reaction equation
[OH:1][C:2]([CH2:10][CH2:11][CH3:12])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5].N1C=CN=C1.[CH3:18][Si:19]([CH3:22])([CH3:21])Cl.CCOCC>CN(C)C=O.O>[CH3:18][Si:19]([CH3:22])([CH3:21])[O:1][C:2]([CH2:10][CH2:11][CH3:12])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 6397ChlorotrimethylsilaneHCID 205539704-Hydroxy-4-n-propyl-1-octyne

Product 1

HCID 20553968(+/-) 4-Trimethylsilyloxy-4-n-propyl-1-octyne

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

16.8 Grams of 4-hydroxy-4-n-propyl-1-octyne is dissolved in 100 ml of dimethylformamide and treated with 8 g of imidazole and then with 12 g of trimethylchlorosilane. The reaction mixture was stirred at room temperature for 1 hour and then poured into a mixture of ether and water. The organic layer was washed with water 3-4 times, dried over sodium sulfate, and stripped of solvent. Distillation of the residue gave the title product as a colorless liquid.

Workup

  1. washThe organic layer was washed with water 3-4 times
  2. dry with materialdried over sodium sulfate
  3. distillationDistillation of the residue

Sources & evidence

ORD record
ord-362273ef0d074c07bc3b70c8ca2a5215
Source dataset
uspto-grants-1982_01
Patent number
US04312994

Reaction notes

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