Sodium Hydroxide → 1-(3-(Hydroxymethyl)isoxazol-5-yl)ethanone
Reaction equation
[CH3:1][C:2]1([C:7]2[O:11][N:10]=[C:9]([CH2:12][OH:13])[CH:8]=2)OCC[O:3]1.[OH-].[Na+]>CO>[OH:13][CH2:12][C:9]1[CH:8]=[C:7]([C:2](=[O:3])[CH3:1])[O:11][N:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of the carbinol 319 (2.39 g, 12.9 mmol) in MeOH (30 mL) 10% HCl (30 mL) was added. The reaction mixture was stirred at 70° C. for 18 hours, cooled and neutralized to pH 6 using 1M NaOH solution. MeOH was evaporated and the resulting aqueous phase was extracted with EtOAc. The organic layer was washed with brine, dried under MgSO4 and concentrated under reduced pressure to produce the title compound as a beige solid (1.67 g, 92% yield), which was used for next step without further purification. 1H NMR (DMSO-d6) δ (ppm): 7.25 (s, 1H), 5.62 (t, J=6.1 Hz, 1H), 4.56 (d, J=5.9 Hz, 2H), 2.56 (s, 3H). MS (m/z): 141.12 (calc) 142.1 (MH+) (found)