Reacción #994693

Ecuación de reacción

sulfite

2,2-bis(hexyloxy)propanyl ethyl sulfite

water

→

2,2-bis(hexyloxy)propanyl ethyl sulfate

Rendimiento 91.0%

Disolventes

MeCN

CH2Cl2

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente