تفاعل #2175487

معادلة التفاعل

alcohol

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

pyridine

ethyl chlorosulfite

→

2,2-bis(hexyloxy)propanyl ethyl sulfite

المردود 88.0%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction is quenched with water (100 mL)
2. 2
   استخلاصextracted with CH2Cl2 (2×100 mL)
3. 3
   غسيلThe combined organic layers are washed with HCl (1N, 100 mL), 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 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.

المصدر