Methyl iodide → HCID 68085721, compound

HRID 2369745Notes

Reaction equation

HRID 2369745 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:3]=1.[CH:14]([N-]C(C)C)(C)C.[Li+].CI.[Cl-].[NH4+]>C1COCC1.CCOC(C)=O>[CH2:1]([C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:3]=1)[CH3:14]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 770264-Methyl-2-phenylpyridineHCID 2724682Lithium diisopropylamide

Product 1

HCID 68085721HCID 68085721, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To 4-methyl-2-phenylpyridine (8 g, 47.3 mmol) in dry THF (150 mL) at −78° C. was added dropwise lithium diisopropylamide (LDA) (30.7 mL, 61.5 mmol). The dark solution was stirred for 3 h at −78° C. and then CH3I was added (4.1 mL, 66.2 mmol) dropwise. The reaction mixture was allowed to slowly warm to room temperature overnight. Ammonium chloride solution and EtOAc were added and the reaction transferred to a reparatory funnel. The layers were separated, washing the aqueous twice with EtOAc and combined organics once with water. After removal of the solvent, the crude product was chromatographed on silica gel with 9/1 (v/v) hexane/EtOAc to give 5.5 g (63.5%) of 4-ethyl-2-phenylpyridine. HPLC purity: 99.0%.

Workup

  1. temperatureto slowly warm to room temperature overnight
  2. customthe reaction transferred to a reparatory funnel
  3. customThe layers were separated
  4. washwashing the aqueous twice with EtOAc
  5. customAfter removal of the solvent
  6. customthe crude product was chromatographed on silica gel with 9/1 (v/v) hexane/EtOAc

Sources & evidence

ORD record
ord-0379dad2e76242cbaab19154c48654dd
Source dataset
uspto-grants-2014_04
Patent number
US08709615B2

Reaction notes

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