Methyl iodide → 2-Isopropylpyridine

HRID 1689422Notes

Reaction equation

HRID 1689422 reaction equation
[CH2:1]([Li])CCC.[CH2:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH3:7].CI>O1CCCC1>[CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:1])[CH3:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 75232-EthylpyridineHCID 178418339Butyllithium

Product 1

HCID 695232-Isopropylpyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of butyllithium (1.6M in hexanes, 50 mL) was added dropwise over 20 min to a solution of 2-ethylpyridine (9.34 mL) in tetrahydrofuran (50 mL) at −70° C. The mixture was stirred for 2 h then methyl iodide (5 mL) was added dropwise over 15 min. The resulting orange slurry was allowed to warm to RT and stirred overnight. The solvent was evaporated and the residue diluted with diethylether (100 mL). The organic layer was washed with water (2×100 mL) and brine (100 mL), then dried over sodium sulphate, filtered and evaporated to give the subtitled compound as a yellow oil. Yield 9.1 g.

Workup

  1. stirringstirred overnight
  2. customThe solvent was evaporated
  3. additionthe residue diluted with diethylether (100 mL)
  4. washThe organic layer was washed with water (2×100 mL) and brine (100 mL)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-b3f6c88eb6dd46e7b28f54f8d94940d0
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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