Hydrochloric Acid → 854758-37-5

HRID 576056Notes

Reaction equation

HRID 576056 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([C:15]1[N:20]=[C:19]([C:21]#N)[CH:18]=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].Cl.[O:24]1CCCC1>C(OCC)(=O)C>[C:11]([C:15]1[N:20]=[C:19]([CH:21]=[O:24])[CH:18]=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 21075124HCID 21075124, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 58790019854758-37-5

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Diisobutylaluminum hydride (1.02 mol/L toluene solution, 23.5 mL, 24.1 mmol) was added to a solution of 6-tert-butylpyridine-2-carbonitrile obtained (2.57 g, 16.0 mmol) in tetrahydrofuran (20 mL) under a nitrogen atmosphere at −78° C., and the mixture was stirred for 1.5 hr while cooling in ice. To the reaction mixture was added 1 mol/L hydrochloric acid, and the mixture was diluted with ethyl acetate and stirred at room temperature for 45 min. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The desiccant was filtered off and then the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane only→hexane:ethyl acetate=4:1) to afford the title compound as a yellow oil (1.71 g).

Workup

  1. temperaturewhile cooling in ice
  2. stirringstirred at room temperature for 45 min
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe desiccant was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane only→hexane

Sources & evidence

ORD record
ord-4acdbc7a78f8410abe864737dbf52d52
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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