Tetrahydrofuran ethanol → (5-(2-Methyl-1,3-dioxolan-2-yl)isoxazol-3-yl)methanol
Reaction equation
[CH3:1][C:2]1([C:7]2[O:11][N:10]=[C:9]([C:12](OCC)=[O:13])[CH:8]=2)[O:6][CH2:5][CH2:4][O:3]1.CCO.C1COCC1>O>[CH3:1][C:2]1([C:7]2[O:11][N:10]=[C:9]([CH2:12][OH:13])[CH:8]=2)[O:6][CH2:5][CH2:4][O:3]1Participants
4
Procedure
To a solution of the dioxolane 318 (3.14 g, 13.8 mmol) in a 1:2 mixture of EtOH-THF (45 mL) NaBH4 (0.68 g, 18.0 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours, treated with water and the organic solvents were evaporated. The aqueous phase was extracted with EtOAc and combined organic layers were successively washed with H2O and brine, dried over MgSO4 and concentrated under reduced pressure to afford the title compound as oil (2.39 g, 93% yield) which was used for next step without further purification. 1H NMR (DMSO-d6) δ (ppm): 6.43 (s, 1H), 5.47 (t, J=5.9 Hz, 1H), 4.47 (d, J=5.9 Hz, 2H), 4.06-4.02 (m, 2H), 3.94-3.90 (m, 2H), 1.66 (s, 3H). MS (m/z): 185.18 (calc) 186.1 (MH+) (found).