Methanol → 2-(5-(Benzyloxy)pyridin-2-yl)acetic acid

HRID 1796481Notes

Reaction equation

HRID 1796481 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]#N)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:18].[Na+].C[OH:21]>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([OH:21])=[O:18])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887Methanol2×HCID 14798Sodium HydroxideHCID 221813855-Benzyloxy-2-cyanomethylpyridine

Product 1

HCID 221813662-(5-(Benzyloxy)pyridin-2-yl)acetic acidYield 89%

Procedure

To a solution of 1.45 g (6.46 mmol) [5-(benzyloxy)-2-pyridinyl]acetonitrile (obtained in 6 steps from 6-methyl-3-pyridinol, see: W. M. Golebiewski and J. T. Wrobel, Bull. Pol. Acad. Sci., 1990, 38, 17) in MeOH (9 mL) was added 25% NaOH (3 mL). The reaction mixture was stirred at reflux for 48 h. After being cooled, most of the MeOH was removed in vacuo, water (10 mL) was added and the aqueous solution was washed with diethyl ether (2×10 mL) followed by acidification (pH ˜6.0). The mixture was extracted with EtOAc (3×20 mL), dried over MgSO4 and concentrated to give pale yellow crystals (1.4 g, 89%). MS (ESI) (M+H)+=244.

Workup

  1. temperatureat reflux for 48 h
  2. customwas removed in vacuo, water (10 mL)
  3. additionwas added
  4. washthe aqueous solution was washed with diethyl ether (2×10 mL)
  5. extractionThe mixture was extracted with EtOAc (3×20 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-38cc3ac55b3a499994494aef66ad020f
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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