Ethanol → Ethyl 5-(hydroxymethyl)picolinate
반응식
[BH4-].[Na+].[Cl-].[Ca+2].[Cl-].C(O[C:9]([C:11]1[CH:12]=[CH:13][C:14]([C:17]([OH:19])=[O:18])=[N:15][CH:16]=1)=[O:10])C.S(=O)(=O)(O)O.[CH2:25](O)[CH3:26]>>[OH:10][CH2:9][C:11]1[CH:12]=[CH:13][C:14]([C:17]([O:19][CH2:25][CH3:26])=[O:18])=[N:15][CH:16]=1참가 물질
6
실험 절차
0.636 g of sodium borohydride was added to 22 mL of ice-cooled ethanol, to which a solution of 1.09 g of calcium chloride in 14 mL of ethanol was added dropwise, followed by addition of 1.20 g of 5-(ethoxycarbonyl)-2-pyridinecarboxylic acid ½ calcium salt, and this mixture was stirred for one hour at room temperature. The reaction mixture, to which 2.8 mL of concentrated sulfuric acid was added, was stirred for 6 hours while heating it under reflux. The reaction mixture was cooled to room temperature and concentrated under reduced pressure followed by successive addition of a saturated aqueous solution of sodium hydrogen carbonate and chloroform, and then the organic phase was separated therefrom. The resultant organic phase was washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure to yield 0.34 g of ethyl 5-(hydroxymethyl)-2-pyridinecarboxylate as light yellow solid.