Potassium borohydride → 1-(6-[1,3]Dioxolan-2-yl-pyridin-2-yl)ethanol
Reaction equation
[BH4-].[K+].[O:3]1[CH2:7][CH2:6][O:5][CH:4]1[C:8]1[N:13]=[C:12]([C:14](=[O:16])[CH3:15])[CH:11]=[CH:10][CH:9]=1>CO>[O:3]1[CH2:7][CH2:6][O:5][CH:4]1[C:8]1[N:13]=[C:12]([CH:14]([OH:16])[CH3:15])[CH:11]=[CH:10][CH:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
0.50 g of potassium borohydride (9.27 mmol) is added in portions to a solution of 0.90 g of 1-(6-[1,3]dioxolan-2-yl-pyridin-2-yl)ethanone (4.66 mmol) in 15 ml of methanol. The mixture is stirred for 12 hours at room temperature and then methanol is evaporated off and the residue is taken up in chloroform. The organic phase is washed with water and then dried over sodium sulfate, filtered, and concentrated under vacuum. 0.70 g of a pale yellow oil is obtained, which oil is used in the next stage without further purification. 1H NMR (CDCl3) δ: 1.47 (d, 3H); 1.84 (s, 1H(exchangeable)); 4.11 (m, 4H); 4.88 (m, 1H); 5.82 (s, 1H); 7.25 (d, 1H); 7.41 (d, 1H); 7.75 (t, 1H).