Imidazole → HCID 21831156, compound

HRID 1601124Notes

Reaction equation

HRID 1601124 reaction equation
[C:1](#[N:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)O.N1C=CN=C1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].CN(C=[O:28])C>>[O:28]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:2][C:1]#[N:10])[Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

5

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 10758MandelonitrileHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 21831156HCID 21831156, compoundYield 82%

Conditions

Temperature
35 °C

Procedure

Mandelonitrile (50 g, 0.38 moles) and imidazole (64 g, 0.94 moles) were dissolved in DMF (100 cm3) and the resulting solution cooled in an ice-water bath. tert-Butyldimethylsilyl chloride (68 g, 0.45 moles) was then added portionwise over a period of 20 minutes. The flask contents were then warmed to 35° C. and stirred at that temperature for 18 hours. The reaction mixture was then cooled and partitioned between ethyl acetate (3×100 cm3) and deionised water (100 cm3). The combined organic fractions were then washed with brine (100 cm3), dried over anhydrous magnesium sulphate and concentrated under reduced pressure to give the crude product as a yellow oil. Flash chromatography (600 g kieselgel 60 silica) eluting with 20% dichloromethane in pentane gave the title compound as an oil (77 g, 0.31 moles, 82%), δH (300 MHz;CDCl3) 0.1 (3H, s), 0.2 (3H, s), 1.0 (9H, s), 5.5 (1H, s), and 7.4 (5H, m).

Workup

  1. temperaturethe resulting solution cooled in an ice-water bath
  2. temperatureThe reaction mixture was then cooled
  3. custompartitioned between ethyl acetate (3×100 cm3) and deionised water (100 cm3)
  4. washThe combined organic fractions were then washed with brine (100 cm3)
  5. dry with materialdried over anhydrous magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product as a yellow oil
  8. washFlash chromatography (600 g kieselgel 60 silica) eluting with 20% dichloromethane in pentane

Sources & evidence

ORD record
ord-0d9c1e657bf84af785357edbb1c3ae72
Source dataset
uspto-grants-1999_11
Patent number
US05977142

Reaction notes

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