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

HRID 2104269Notes

Reaction equation

HRID 2104269 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-b05a71cbcd304757ba309d5d710f74c9
Source dataset
uspto-grants-2009_08
Patent number
US07576239B2

Reaction notes

Loading…