Imidazole → 4-Difluoromethyl-4-trimethylsiloxy-1-octyne

HRID 903669Notes

Reaction equation

HRID 903669 reaction equation
[F:1][CH:2]([F:12])[C:3]([OH:11])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:4][C:5]#[CH:6].N1C=CN=C1.[CH3:18][Si:19]([CH3:22])([CH3:21])Cl.C(=O)(O)[O-].[Na+]>CCCCCC.CN(C)C=O>[F:1][CH:2]([F:12])[C:3]([O:11][Si:19]([CH3:22])([CH3:21])[CH3:18])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:4][C:5]#[CH:6]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 127861894-Difluoromethyl-4-hydroxy-1-octyne

Product 1

HCID 217647864-Difluoromethyl-4-trimethylsiloxy-1-octyne

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

A solution of 11.5 g. of 4-difluoromethyl-4-hydroxy-1-octyne and 11.32 g. of imidazole in 45 ml. of dimethylformamide is cooled in an ice bath under nitrogen. A 10.3 ml. portion of trimethylchlorosilane is added using a syringe over a 15 minute period. The mixture is stirred in the ice bath for one hour and then overnight at room temperature. The solution is diluted with hexane and then poured into saturated aqueous sodium bicarbonate solution. The hexane solution is separated, washed with aqueous sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate and the solvents are evaporated to dryness giving the desired product as a colorless liquid.

Workup

  1. customover a 15 minute
  2. customovernight
  3. customat room temperature
  4. customThe hexane solution is separated
  5. washwashed with aqueous sodium bicarbonate solution and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvents are evaporated to dryness

Sources & evidence

ORD record
ord-768500c4d36241c0ba49466df49678f0
Source dataset
uspto-grants-1980_10
Patent number
US04228298

Reaction notes

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