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

反応式

[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

参加物

反応物 3

HCID 887Methanol2 回

HCID 14798Sodium Hydroxide

HCID 221813855-Benzyloxy-2-cyanomethylpyridine

生成物 1

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

実験手順

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.