Methyl iodide → HCID 68085721, compound

HRID 713566Notes

Reaction equation

HRID 713566 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-df6712bf113d4f38897d22436a4e757d
Source dataset
uspto-grants-2015_11
Patent number
US09184397B2

Reaction notes

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