反応 #1256731

反応方程式

HPTS

H2SO4

→

1

sodium 3-hydroxypyrene-5-sulfonate

溶媒

water

反応条件

後処理

1. 1
   その他equipped with a magnetic stirring bar
2. 2
   温度to cool at ambient temp for 10 min
3. 3
   抽出The mixture was extracted with isopropyl acetate (200 mL×4)
4. 4
   濃縮concentrated in vacuo
5. 5
   workup.ADDITIONThe residue was mixed with silica gel (3 g)
6. 6
   その他crushed into a fine powder
7. 7
   その他dry
8. 8
   その他The residue was purified via gradient elution

実験手順

Referring to Scheme 4, a 50-mL round bottom flask equipped with a magnetic stirring bar was charged with HPTS (9.5 mmols, 5 g) and 30% H2SO4 (35 mL). The mixture was heated at 150° C. for 20 min and then allowed to cool at ambient temp for 10 min. The solution was poured into 100 g of crushed ice and diluted to 200 mL with water. The mixture was extracted with isopropyl acetate (200 mL×4) and concentrated in vacuo. The residue was mixed with silica gel (3 g) and crushed into a fine powder and dry loaded onto a Biotage 40 M cartridge. The residue was purified via gradient elution using 5% MeOH: (5% NEt3:CH2Cl2) to 15% MeOH: (5% NEt3:CH2Cl2) to give the triethylamine salt of 1 (0.281 g). The salt was treated with 1 M HCl and extracted with isopropyl acetate and the isopropyl acetate layer dried over MgSO4 and concentrated in vacuo to give 1 as a brown/green foam. Synthesis of 1 was reported previously by E. Tietze and O. Bayer 1939 Ann 540:189-210. TLC (MeOH: CH2Cl2:NEt3, 2:7:1) Rf=0.23. 1H NMR (500 MHz, CD3OD) δ7.94 (t, J=7.6 Hz, 1H), 7.97 (d, J=9.4 Hz, 1H), 8.02 (d, J=9.2 Hz, 1H), 8.11 (t, J=7.7 Hz, 2H), 8.25 (s, 1H), 8.39 (d, J=9.1 Hz, 1H), 8.98 (d, J=9.3 Hz, 1H).

出典