Methanol → 2-(5-(Benzyloxy)pyridin-2-yl)acetic acid
Reaktionsgleichung
[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]=1Komponenten
4
Versuchsvorschrift
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.