3-Pyridinemethanol → Ethyl 2-((pyridin-3-yl)methoxy)acetate

HRID 446904Notes

Reaction equation

HRID 446904 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][OH:10])[CH:4]=1.Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][O:10][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]=1

Participants

7

Reactant 3

HCID 75103-PyridinemethanolHCID 7748Ethyl bromoacetateHCID 24758Sodium hydride

Product 1

HCID 19261392Ethyl 2-((pyridin-3-yl)methoxy)acetate

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(Step 4-i) Sodium hydride (60%) (0.44 g, 11 mmol) was added to a solution of (pyridin-3-yl)methanol (1.09 g, 10 mmol) in THF. The reaction mixture was stirred at room temperature for 10 min and ethyl bromoacetate (1.8 g, 11 mmol) was added, followed by the addition of 20 mg of tetrabutyl ammonium iodide. The reaction mixture was stirred overnight, diluted with ethyl acetate/saturated sodium bicarbonate, and the organic layer was dried over sodium sulfate. The solution was concentrated to an oil, which was purified by silica gel column chromatography to give the product, ethyl 2-((pyridin-3-yl)methoxy)acetate, as a brown oil (0.63 g, 3.2 mmol, 32% yield): 1H-NMR (500 MHz, DMSO-d6) 8.63 (d, J=1.8 Hz, 1H), 8.59 (dd, J=1.5, 4.8 Hz, 1H), 7.79 (d, J=7.8 Hz, 1H), 7.34 (dd, J=4.9, 7.7 Hz, 1H), 4.68 (s, 2H), 4.26 (q, J=7.1 Hz, 2H), 4.15 (s, 2H), 1.32 (t, J=7.1 Hz, 3H).

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. concentrationThe solution was concentrated to an oil, which
  4. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ceb1df5fd3f14e278b5e4eaa7dcdd630
Source dataset
uspto-grants-2013_07
Patent number
US08481538B2

Reaction notes

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