Imidazole → HCID 21764788, compound

HRID 126717Notes

Reaction equation

HRID 126717 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]([OH:11])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:4][C:5]#[CH:6].N1C=CN=C1.[CH3:19][Si:20](Cl)([CH3:22])[CH3:21]>CN(C)C=O>[F:1][C:2]([F:12])([F:13])[C:3]([O:11][Si:20]([CH3:22])([CH3:21])[CH3:19])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:4][C:5]#[CH:6]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 12786190HCID 12786190, compound

Product 1

HCID 21764788HCID 21764788, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 4.99 g. of 4-trifluoromethyl-4-hydroxy-1-octyne and 5.65 g. of imidazole in 28 ml. of dry dimethylformamide, under argon, is cooled in an ice bath and then treated with 5.2 ml. of trimethylsilyl chloride by dropwise addition over a period of about 20 minutes. After an additional 15 minutes at ice bath temperature, the reaction mixture is stirred at room temperature overnight. The mixture is then poured into approximately 150 ml. of hexane and washed with small portions of ice cold water and saturated saline solution. The solution is dried over anhydrous magnesium sulfate and evaporated under reduced pressure to give the desired product.

Workup

  1. additiontreated with 5.2 ml
  2. additionThe mixture is then poured into approximately 150 ml
  3. washof hexane and washed with small portions of ice cold water and saturated saline solution
  4. dry with materialThe solution is dried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-53df4e6b186e4eb5a9205d2deecb260f
Source dataset
uspto-grants-1981_03
Patent number
US04254036

Reaction notes

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