Water → 3-[(Cyclopent-3-en-1-yl)methyl]pyridin-2(1H)-one

HRID 1727186Notes

Reaction equation

HRID 1727186 reaction equation
[CH:1]1([CH2:6][C:7]2[C:8]([O:13]C)=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:5][CH:4]=[CH:3][CH2:2]1.[I-].[Na+].Cl[Si](C)(C)C.O>C(#N)C.C(OCC)(=O)C>[CH:1]1([CH2:6][C:7]2[C:8](=[O:13])[NH:9][CH:10]=[CH:11][CH:12]=2)[CH2:2][CH:3]=[CH:4][CH2:5]1

Participants

7

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 598378653-[(Cyclopent-3-en-1-yl)methyl]-2-methoxypyridine

Product 1

HCID 598378373-[(Cyclopent-3-en-1-yl)methyl]pyridin-2(1H)-oneYield 100%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cloudy dispersion containing 3-(cyclopent-3-en-ylmethyl)-2-(methyloxy)pyridine (Preparation 28, 2.1 g, 11.1 mmol) and sodium iodide (4.1 g, 27.8 mmol) in anhydrous acetonitrile (25 ml) was added chlorotrimethylsilane (3.0 g, 27.8 mmol). A white precipitate formed which was stirred for 30 min at room temperature and then for 1 h at 70° C. The reaction mixture was cooled to room temperature and water was added, followed by ethyl acetate (200 ml), the organic layer washed with water (4×) and then with sodium hydrogen carbonate solution and brine before drying (Na2SO4) to give the title compound as a yellow solid (1.93 g, 100%).

Workup

  1. customA white precipitate formed which
  2. waitfor 1 h at 70° C
  3. temperatureThe reaction mixture was cooled to room temperature
  4. washthe organic layer washed with water (4×)
  5. dry with materialwith sodium hydrogen carbonate solution and brine before drying (Na2SO4)

Sources & evidence

ORD record
ord-fd63a9b3c8d540aba352e74c41279b91
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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