Sodium borohydride → 2-Cyano-5-hydroxymethylpyridine
Reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[N:7][CH:6]=1)C.[BH4-].[Na+]>CO>[OH:3][CH2:4][C:5]1[CH:6]=[N:7][C:8]([C:11]#[N:12])=[CH:9][CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of ethyl-6-cyanonicotinate (prepared as per T. Sakamoto, S. Kaneda, S. Nishimura and H. Yamanaka Chem. Pharm. Bull. 1985, 33, 565) (1.58 g, 8.97 mmol) in MeOH (40 mL) was added NaBH4 (1.00 g, 26.4 mmol) and the reaction stirred at room temperature for 8 h. After removal of the solvent, the residue was taken up in 15% NaOH (5 mL) and stirred for 20 min. The mixture was then extracted repeatedly with CH2Cl2, and the combined organic fractions were dried (Na2SO4), filtered and concentrated under reduced pressure. Purification of the residue by chromatography on silica gel (EtOAc/hexanes, 1:1) afforded 3-hydroxymethyl-6-cyanopyridine (414 mg, 34%). 1H NMR (CDCl3) δ 5.16 (s, 2H), 7.69 (d, 1H, J=6.8 Hz), 7.84 (d, 1H, J=6.8 Hz), 8.71 (s, 1H).