1,3,4-Trimethylpyridin-1-ium iodide → 2-Benzyl-1,3,4-trimethyl-1,2-dihydropyridine

HRID 1707599Notes

Reaction equation

HRID 1707599 reaction equation
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[CH3:11][N+:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:19])[CH:13]=1>C1COCC1>[CH2:1]([CH:13]1[C:14]([CH3:19])=[C:15]([CH3:18])[CH:16]=[CH:17][N:12]1[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 125431661,3,4-Trimethylpyridin-1-ium iodideHCID 178418336HCID 178418336, compound

Product 1

HCID 157330592-Benzyl-1,3,4-trimethyl-1,2-dihydropyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.02M of benzylmagnesium chloride (2M solution) in THF was added portionwise 300 g (20 g portions) of 1,3,4-trimethylpyridinium iodide. The reaction mixture was stirred at room temperature for 18 hrs. The THF was evaporated at reduced pressure, and the resulting residue was poured into iced saturated NH4Cl. The mixture was extracted with ether and the ether solution washed with additional saturated NH4Cl. The ether solution was dried over magnesium sulfate and evaporated to dryness at reduced pressure to afford 338 g of crude 2-benzyl-1,3,4-trimethyl-1,2-dihydropyridine.

Workup

  1. customThe THF was evaporated at reduced pressure
  2. additionthe resulting residue was poured into iced saturated NH4Cl
  3. extractionThe mixture was extracted with ether
  4. washthe ether solution washed with additional saturated NH4Cl
  5. dry with materialThe ether solution was dried over magnesium sulfate
  6. customevaporated to dryness at reduced pressure

Sources & evidence

ORD record
ord-8af43e54297642a996d015e772d2fe70
Source dataset
uspto-grants-1994_10
Patent number
US05354758

Reaction notes

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