Sodium borohydride → [3,3'-Bipyridin]-5-ylmethanol
Reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:9]=[N:10][CH:11]=1)=O)C.[BH4-].[Na+]>C(O)C>[N:10]1[CH:11]=[C:6]([CH2:4][OH:3])[CH:7]=[C:8]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of [3,3′]bipyridinyl-5-carboxylic acid ethyl ester (1 eq) in ethanol was added sodium borohydride (2 eq) at room temperature. The reaction mixture was heated in a 50° C. oil bath for 60 minutes and then quenched by addition of H2O. Once the reaction solvent was removed in vacuo, a solution of the residue in dichloromethane was washed with NaCl(sat), dried over sodium sulfate, filtered and concentrated. The crude solid was purified by flash chromatography using a solvent gradient of 95% DCM, 5% MeOH and 0.1% TEA to yield [3,3′]bipyridinyl-5-yl-methanol (34%). MH+(187).