反応 #57331

反応方程式

chlorosulfonic acid

3,4-diphenyl-2-(5H )-furanone

→

4-phenyl-2-(5H )-furanone

収率 98.3%

溶媒

dichloromethane

反応条件

後処理

1. 1
   温度maintained at that temperature for 16 hours
2. 2
   その他quenched into ice water
3. 3
   その他The phases were separated
4. 4
   抽出the aqueous phase extracted with dichloromethane
5. 5
   抽出the combined dichloromethane extract
6. 6
   乾燥was dried over anhydrous MgSO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated in vacuo
9. 9
   workup.ADDITIONThe residue was diluted with dichloromethane
10. 10
    workup.ADDITIONadded to excess concentrated NH4OH
11. 11
    その他The phases were separated
12. 12
    抽出the aqueous phase was extracted with dichloromethane
13. 13
    抽出The organic extract
14. 14
    乾燥was dried over anhydrous MgSO4
15. 15
    ろ過filtered
16. 16
    濃縮concentrated in vacuo
17. 17
    その他to give a white solid
18. 18
    その他that was crystallized from aqueous ethanol

実験手順

To 20 mL of stirring chlorosulfonic acid cooled to −5° C. was added 3,4-diphenyl-2-(5H )-furanone (Step 1)(3.160 g, 13.4 mmol) portion-wise over 30 minutes. The solution was warmed to room temperature and maintained at that temperature for 16 hours. The reaction mixture was diluted with dichloromethane and quenched into ice water. The phases were separated and the aqueous phase extracted with dichloromethane, the combined dichloromethane extract was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was diluted with dichloromethane and added to excess concentrated NH4OH. The mixture was stirred for 1 hour. The phases were separated and the aqueous phase was extracted with dichloromethane. The organic extract was dried over anhydrous MgSO4, filtered and concentrated in vacuo to give a white solid that was crystallized from aqueous ethanol to afford pure 3-[(4-aminosulfonyl)phenyl)]-4-phenyl-2-(5H )-furanone (2.110 g, 50%): mp 225.5-226.5° C. 1H NMR (CDCl3/300 MHz) 7.79 (d, 2H, J=8.4 Hz), 7.41 (d, 2H, J=8.4 Hz), 6.38 (brs, 2H), 5.09 (s, 2H). FABLRMS m/z 316 (m+H). Anal. Calc'd for C16H13NO4S: C, 60.94; H, 4.16; N, 4.44. Found: C, 60.86; H, 4.18; N, 4.40.

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