Hydrochloric Acid → HCID 576396, compound

HRID 1720739Notes

Reaction equation

HRID 1720739 reaction equation
Cl[Mg][CH2:3][CH:4]([CH3:6])[CH3:5].[C:7](#N)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[CH3:16]COCC>>[CH3:5][CH:4]([CH3:6])[CH2:3][C:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[CH2:16]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 7505BenzonitrileHCID 178418368HCID 178418368, compound

Product 1

HCID 576396HCID 576396, compoundYield 83%

Procedure

Chloro-(2-methylpropyl)magnesium (150 ml, 0.300 mol, from Aldrich) was added over 20 minutes to a solution of benzonitrile (10.21 ml, 0.100 mol, from Aldrich) in ether (150 ml), stirring under argon at room temperature. The solution was allowed to stir under argon at room temperature for 18 hours. The reaction mixture was then cooled to 0° C. and 1.2N HCl (125 ml) was added. The aqueous layer was extracted with ether (twice), and the organic layers were combined and washed with brine and dried over MgSO4, filtered and concentrated to a yellow oil. The oil was purified by flash chromatography on Merck silica gel in 2% EtOAc in hexane. Fractions containing the product were combined and concentrated to afford the title compound as a yellow oil (13.305 gm, 83%).

Workup

  1. stirringto stir under argon at room temperature for 18 hours
  2. temperatureThe reaction mixture was then cooled to 0° C.
  3. extractionThe aqueous layer was extracted with ether (twice), and the organic layers
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to a yellow oil
  8. customThe oil was purified by flash chromatography on Merck silica gel in 2% EtOAc in hexane
  9. additionFractions containing the product
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f5692724c5984d8890cdbfbabd4c7942
Source dataset
uspto-grants-1996_04
Patent number
US05506219

Reaction notes

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