تفاعل #2175488

معادلة التفاعل

sulfite

2,2-bis(hexyloxy)propanyl ethyl sulfite

water

→

2,2-bis(hexyloxy)propanyl ethyl sulfate

المردود 91.0%

المذيبات

MeCN

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe mixture is filtered through Celite
2. 2
   استخلاصextracted with CH2Cl2 (2×200 mL)
3. 3
   غسيلThe combined organic layers are washed with saturated NaHCO3 (100 mL), brine (100 mL)
4. 4
   تجفيفdried over anhydrous sodium sulfate
5. 5
   أخرىThe solvent is removed
6. 6
   أخرىthe residue is purified by silica gel chromatography (1→10% ethyl acetate/hexane)

الإجراء التجريبي

To a solution of sulfite 6 (24.5 g, 69.5 mmol) in MeCN (200 mL), CH2Cl2 (200 mL) and water (300 mL) is added NaIO4 (29.7 g, 139.0 mmol) and RuCl3 (10 mg, 0.05 mmol). The mixture is stirred at 23° C. for 5 hours. The mixture is filtered through Celite and extracted with CH2Cl2 (2×200 mL). The combined organic layers are washed with saturated NaHCO3 (100 mL), brine (100 mL) and dried over anhydrous sodium sulfate. The solvent is removed and the residue is purified by silica gel chromatography (1→10% ethyl acetate/hexane) to give 2,2-bis(hexyloxy)propanyl ethyl sulfate 7 (23.3 g, 91%) as a colorless oil: Rf (15% EtOAc/hexane)=0.41; IR (thin film, cm−1) 2931, 2860, 1737, 1467, 1403, 1380, 1196, 1179, 1012, 925, 858; 1H NMR (600 MHz, CDCl3) δ 4.34 (q, J=7.2 Hz, 2H), 4.09 (s, 2H), 3.43 (ddd, J=9.0, 7.2, 6.6 Hz, 2H), 3.38 (ddd, J=9.0, 7.2, 6.6 Hz, 2H), 1.51 (m, 4H), 1.40 (t, J=7.2 Hz, 3H), 1.37 (s, 3H), 1.34-1.24 (m, 12H), 0.86 (t, J=7.2 Hz, 6H); 13C NMR (150 MHz, CDCl3) δ 98.2, 72.4, 69.7, 60.9, 31.6, 29.8, 25.9, 22.6, 20.8, 14.5, 14.0.

المصدر