Imidazole → HCID 21764790, compound

HRID 848901Notes

Reaction equation

HRID 848901 reaction equation
[F:1][CH2:2][C:3]([OH:11])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:4][C:5]#[CH:6].N1C=CN=C1.CN(C)C=O.[CH3:22][Si:23]([CH3:26])([CH3:25])Cl>CCCCCC>[F:1][CH2:2][C:3]([O:11][Si:23]([CH3:26])([CH3:25])[CH3:22])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:4][C:5]#[CH:6]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 12786188HCID 12786188, compound

Product 1

HCID 21764790HCID 21764790, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a solution of 4.38 g. of 4-fluoromethyl-4-hydroxy-1-octyne and 4.8 g. of imidazole in 19 ml. of dimethylformamide, cooled in an ice bath under nitrogen is added 4.5 ml. of trimethylchlorosilane via a syringe during a few minutes. The mixture is stirred in the ice bath for 30 minutes and then at room temperature under nitrogen overnight. The solution is poured into hexane, washed with saturated aqueous sodium bicarbonate, water, then brine and dried over anhydrous sodium sulfate. The solvents are removed in vacuo giving the product as a colorless liquid.

Workup

  1. additionis added 4.5 ml
  2. customat room temperature
  3. customovernight
  4. washwashed with saturated aqueous sodium bicarbonate, water
  5. dry with materialbrine and dried over anhydrous sodium sulfate
  6. customThe solvents are removed in vacuo

Sources & evidence

ORD record
ord-459e91eacff7490db96c1818679b45e0
Source dataset
uspto-grants-1981_10
Patent number
US04297516

Reaction notes

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