1-Octanol → HCID 22506523, compound

Participants

Reaction Steps

To 3.0 mL of anhydrous triethylamine (23.04 mmol, 30 equiv.) at 0° C. was added 1-octanol (0.10 g 0.77 mmol, 1 equiv.) followed by the addition of 2-pyridylsulfonyl chloride in one portion. The mixture was kept at 0° C. for 3 hours followed by the addition of water (5 mL). The resulting mixture was extracted with diethyl ether (3×50 mL), then the organic extracts were combined and washed with aqueous NaHCO3 solution (50 mL), dried (MgSO4), and concentrated under reduced pressure. Column chromatography (2% EtOAc/Hex) afforded 15 (99%): 1H NMR (CDCl3, 400 MHz) δ 8.68 (d, J=7.0 Hz, 1H, ArH), 7.94 (p, J=8.8 Hz, 2H, ArH), 7.54 (t, J=6.4 Hz, 1H, ArH), 4.26 (t, J=6.7 Hz, 2H, CH2OSO2R), 1.61 (p, J=7.9 Hz, 2H), 1.13 (m, 10H), 0.76 (t, J=7.0 Hz, 3H); MALDI-FTMS 294.1130 (C13H21NO3S+Na+ requires 294.1134).

Provenance & Evidence