Acetonitrile → HCID 67497550, compound

HRID 1628237Notes

Reaction equation

HRID 1628237 reaction equation
C1COCC1.[C:6](#[N:8])[CH3:7].C([Li])CCC.[CH3:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][N:24]=1)[C:18]([O:20]C)=O>CC(O)=O>[CH3:14][C:15]1[CH:16]=[C:17]([C:18](=[O:20])[CH2:7][C:6]#[N:8])[CH:22]=[CH:23][N:24]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8028Tetrahydrofuran2×HCID 11542811Methyl 2-methylisonicotinateHCID 178418339Butyllithium

Product 1

HCID 67497550HCID 67497550, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
-78 °C

Procedure

To a 50 ml flask was added 8 ml of THF, acetonitrile (156 μl, 2.98 mmole), the mixture was cooled to −78° C. and then n-butyllithium (1191 μl, 2.98 mmole, 2.5 m in hexanes) was added. The reaction was stirred for 30 minutes at which time methyl 2-methylisonicotinate 16.1.B (150 mg, 0.99 mmoles) was added as a 2 ml THF solution. After 2 hour at −78° C., 500 μL of AcOH was added and the reaction was warmed to room temperature. The solvent was removed and the crude was purified on a silica gel column (eluting with 2% MeOH in DCM) to give 3-(2-methylpyridin-4-yl)-3-oxopropanenitrile 16.1.C as a light orange solid (170 mg 100% yield).

Workup

  1. temperaturethe reaction was warmed to room temperature
  2. customThe solvent was removed
  3. customthe crude was purified on a silica gel column (eluting with 2% MeOH in DCM)

Sources & evidence

ORD record
ord-514ec62b08674a93a398cd3f43097bf9
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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