Cesium carbonate → 1-{[2-(Trimethylsilyl)ethoxy]methyl}pyridin-4(1H)-one

HRID 1394550Notes

Reaction equation

HRID 1394550 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH3:8][Si:9]([CH2:12][CH2:13][O:14][CH2:15]Cl)([CH3:11])[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:8][Si:9]([CH2:12][CH2:13][O:14][CH2:15][N:5]1[CH:6]=[CH:7][C:2](=[O:1])[CH:3]=[CH:4]1)([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178418642HCID 178418642, compound

Product 1

HCID 140051601-{[2-(Trimethylsilyl)ethoxy]methyl}pyridin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-hydroxypyridine (3.0 g, 32 mmol) and trimethylsilylethoxymethyl chloride (5.5 mL, 32 mmol) in 30 mL of acetonitrile was added cesium carbonate (11 g, 34 mmol). After stirring at room temperature overnight, the reaction mixture was partitioned between brine (100 mL) and ethyl acetate (100 mL). The organic layer was separated and aqueous layer extracted with ethyl acetate (3×100 mL). The combined extracts were dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to give the title compound contaminated with some O-alkylated product. 1H NMR (500 MHz, CD3OD): δ 7.92 (d, 2H), 6.49 (d, 2H), 5.28 (s, 2H), 3.62 (t, 2H), 0.96 (t, 2H), 0.024 (s, 9H).

Workup

  1. customthe reaction mixture was partitioned between brine (100 mL) and ethyl acetate (100 mL)
  2. customThe organic layer was separated
  3. extractionaqueous layer extracted with ethyl acetate (3×100 mL)
  4. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-04516497d4684583920e4bed983728a3
Source dataset
uspto-grants-2008_03
Patent number
US07348456B2

Reaction notes

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