Methyl iodide → 2-Methyl-1-phenyl-2-(pyridin-2-yl)propan-1-one

HRID 575921Notes

Reaction equation

HRID 575921 reaction equation
[C:1]1([C:7](=[O:16])[CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:19]I>C1COCC1>[CH3:9][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)([CH3:19])[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 115502561-Phenyl-2-(pyridin-2-yl)propan-1-one

Product 1

HCID 594074642-Methyl-1-phenyl-2-(pyridin-2-yl)propan-1-oneYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of compound 3 (3.0 g, 14.2 mmol) in THF (10 mL) is added to a suspension of sodium hydride (60%, 0.63 g, 15.6 mmol) in THF (60 mL) at 0° C. The reaction mixture is kept at the same temperature for 2 hours and methyl iodide (0.93 mL, 14.9 mmol) is added at 0° C. The reaction mixture is allowed to warm up to room temperature overnight and then quenched with water. The mixture is separated and the aqueous phase is extracted with ethyl acetate (2×40 mL). The extracts are combined, washed with brine, dried, concentrated and purified by column chromatography (hexane/ethyl acetate 50:1 to 4:1) to give 4 (2.2 g, 69%) as a yellow solid.

Workup

  1. customquenched with water
  2. customThe mixture is separated
  3. extractionthe aqueous phase is extracted with ethyl acetate (2×40 mL)
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated
  7. custompurified by column chromatography (hexane/ethyl acetate 50:1 to 4:1)

Sources & evidence

ORD record
ord-e042da5ffa2b44758f83ce37b7e70a08
Source dataset
uspto-grants-2015_05
Patent number
US09035065B2

Reaction notes

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