Imidazole → HCID 21764790, compound

HRID 903665Notes

Reaction equation

HRID 903665 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-b9c9ece075e044068b0dc5eed725b1f3
Source dataset
uspto-grants-1980_10
Patent number
US04228298

Reaction notes

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