Water → HCID 46945306, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence