Water → HCID 46945306, compound

Temperature

23 °C

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.

1. filtrationThe mixture is filtered through Celite
2. extractionextracted with CH2Cl2 (2×200 mL)
3. washThe combined organic layers are washed with saturated NaHCO3 (100 mL), brine (100 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. customThe solvent is removed
6. customthe residue is purified by silica gel chromatography (1→10% ethyl acetate/hexane)

ORD record

ord-c2e3751aecf7431791fb5c97279bed86

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08232423B2