Reacción #994692

Ecuación de reacción

alcohol

2,2-bis(hexyloxy)propan-1-ol

pyridine

ethyl chlorosulfite

→

2,2-bis(hexyloxy)propanyl ethyl sulfite

Rendimiento 88.0%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction is quenched with water (100 mL)
2. 2
   Extracciónextracted with CH2Cl2 (2×100 mL)
3. 3
   LavadoThe combined organic layers are washed with HCl (1N, 100 mL), 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 alcohol 4 (20.6 g, 79.1 mmol) in CH2Cl2 (200 mL) is added pyridine (8.12 g, 102.8 mmol) and ethyl chlorosulfite (12.2 g, 94.9 mmol). The reaction mixture is stirred at 23° C. for 10 hours. The reaction is quenched with water (100 mL) and extracted with CH2Cl2 (2×100 mL). The combined organic layers are washed with HCl (1N, 100 mL), 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 sulfite 6 (24.5 g, 88%) as a colorless oil: Rf (15% EtOAc/hexane)=0.44; IR (thin film, cm−1) 2932, 2872, 1467, 1379, 1213, 1194, 1176, 1001, 888; 1H NMR (600 MHz, CDCl3) δ 4.11-4.00 (m, 2H), 3.93 (d, J=10.8 Hz, 1H), 3.77 (d, J=10.8 Hz, 1H), 3.42-3.37 (m, 4H), 1.51-1.48 (m, 4H), 1.33 (s, 3H), 1.31-1.24 (m, 15H), 0.85 (t, J=7.2 Hz, 6H); 13C NMR (150 MHz, CDCl3) δ 99.0, 62.9, 60.8, 58.5, 58.3, 31.6, 29.8, 25.9, 22.6, 20.9, 15.3, 14.0.

Fuente