反应详情

Magnesium (granulate) (8.70 g, 358 mmol) was added to a solution of crude 2-methyl-5-(3-((phenylsulfonyl)methyl)oxetan-3-yl)phenol (7.6 g, 23.9 mmol) in MeOH (100 mL). The resulting mixture was stirred for 2 min in an ultrasound bath. The flask was then fitted with a condenser. Stirring was continued for 3 h, at which point the reaction mixture turned cloudy and off white in color. The reaction was exothermic, which caused the solvent to reflux. Water bath was added to lower the reaction mixture temperature to room temperature. The reaction mixture was then stirred overnight and became heterogeneous and pale orange in color. Et2O (525 mL) was added, followed by Na2SO4.10H2O (85 g). The resulting mixture was stirred for 2 h at room temperature and Celite® was then added. The resulting mixture was stirred for another 1 h and filtered through a Buchner funnel packed with Celite®. The cake was washed with EtOAc (2×) and MeOH (1×). The light yellow filtrate was concentrated and the residue was triturated with CHCl3 (220 mL) and filtered. The filtrate was concentrated to provide 2-methyl-5-(3-methyloxetan-3-yl)phenol. 1H NMR (400 MHz, CD2Cl2) δ ppm 7.14 (d, J=7.83 Hz, 1 H) 6.73 (d, J=7.58 Hz, 1 H) 6.69 (d, J=1.77 Hz, 1 H) 4.92 (d, J=5.31 Hz, 2 H) 4.61 (d, J=5.56 Hz, 2 H) 2.26 (s, 3 H) 1.72 (s, 3 H)

1. customThe flask was then fitted with a condenser
2. stirringStirring
3. waitwas continued for 3 h, at which
4. temperatureto reflux
5. additionWater bath was added
6. customto room temperature
7. stirringThe reaction mixture was then stirred overnight
8. stirringThe resulting mixture was stirred for 2 h at room temperature
9. additionCelite® was then added
10. stirringThe resulting mixture was stirred for another 1 h
11. filtrationfiltered through a Buchner funnel
12. washThe cake was washed with EtOAc (2×) and MeOH (1×)
13. concentrationThe light yellow filtrate was concentrated
14. customthe residue was triturated with CHCl3 (220 mL)
15. filtrationfiltered
16. concentrationThe filtrate was concentrated