Sodium borohydride → 2-Pyrimidineethanol, beta,beta-difluoro-
Reaction equation
C([O:3][C:4](=O)[C:5]([F:13])([F:12])[C:6]1[N:11]=[CH:10][CH:9]=[CH:8][N:7]=1)C.[BH4-].[Na+]>CCO>[F:13][C:5]([F:12])([C:6]1[N:7]=[CH:8][CH:9]=[CH:10][N:11]=1)[CH2:4][OH:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of difluoro-pyrimidin-2-yl-acetic acid ethyl ester (1.75 g, 8.65 mmol), as prepared in the previous step (and containing undissolved green precipitate), in anhydrous absolute EtOH (18 mL) was stirred at 0° C. for 5 min, and was then treated with solid NaBH4 (655 mg, 17.3 mmol) in one slow steady portion at 0° C. Bubbles immediately formed, and the solution turned light amber. Stirring continued at 0° C. for 2 h, and the reaction was then quenched with half-saturated NH4Cl (40 mL) and extracted with EtOAc (2×15 mL). The organic phases were combined, washed with saturated NaCl (1×10 mL), dried (Na2SO4), and concentrated to give the title compound as a yellow oil (696 mg, 50%).