Methyl iodide → 6-Methoxymethyl-2,3-diphenyl-pyridine

HRID 12566Notes

Reaction equation

HRID 12566 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:19][OH:20])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CI.[C:23]([O-])([O-])=O.[K+].[K+]>[OH-].[K+].CC(C)=O.O>[CH3:23][O:20][CH2:19][C:10]1[N:11]=[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59338836HCID 59338836, compound2×

Product 1

HCID 250331696-Methoxymethyl-2,3-diphenyl-pyridine

Reagents, catalysts & solvents 3

HCID 14797Potassium HydroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 5,6-diphenylpyridin-2-yl)methanol (Compound 90, 15 mg, 0.06 mmol), MeI (0.1 ml), K2CO3 (50 mg) and KOH (5N, 5 drops) in acetone was heated at 56° C. over night. The mixture was diluted with water and the product was extracted with ethyl acetate. The organic layer was washed with water, and brine, and dried over Na2SO4. The filtered solvent was concentrated in vacuo, and the residue was purified by silica gel chromatography (15% ethyl acetate in hexane) to give title compound as a solid.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with water, and brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe filtered solvent was concentrated in vacuo
  5. customthe residue was purified by silica gel chromatography (15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-46ee8680c7cf4c3cbfe56f6085e9b6e3
Source dataset
uspto-grants-2010_06
Patent number
US07728014B2

Reaction notes

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