4-Hydroxy-3-isobutyryl-6-isopropyl-pyran-2-one → 4-hydroxy-6-(propan-2-yl)-2H-pyran-2-one
반응식
[OH:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[O:5][C:4](=[O:11])[C:3]=1C(=O)C(C)C>OS(O)(=O)=O>[OH:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:9])[CH3:10])[O:5][C:4](=[O:11])[CH:3]=1참가 물질
3
반응 조건
- 온도
- 0 °C
실험 절차
A solution of 4-hydroxy-3-isobutyryl-6-isopropyl-pyran-2-one (10.26 g, 45.8 mmol) in conc. H2SO4 (40 mL) is stirred at 130° C. for 15 min. The dark reaction mixture is then cooled to 0° C., and crushed ice (˜200 g) is added with stirring. The resulting solution is extracted thrice with Et2O, and the combined extracts are dried over Na2SO4 and concentrated. The crude material is purified by flash chromatography on silica gel. Gradient elution with 3:2 hexanes-EtOAc, 1:1 EtOAc-hexanes, 2:1 EtOAc-hexanes, and 3:1 EtOAc-hexanes affords 4-hydroxy-6-isopropyl-pyran-2-one as a light yellow solid. 1H NMR (CDCl3, 300 MHz) δ 11.2 (br, 1H), 6.00 (d, J=1.8 Hz, 1H), 5.58 (d, J=1.8 Hz, 1H), 2.73 (sept, J=6.9 Hz, 1H), 1.22 (d, J=6.9 Hz, 1H) ppm.