Pentaethylene Glycol Dimethanesulfonate synthesis

Yield:109789-39-1 100%

Reaction Conditions:

with triethylamine in dichloromethane at 20; for 22 h;

Steps:

1

MsCl (10.5 mL, 134.44 mmol) was added dropwise to a stirred solution of PEG5-di-OH (12.8 g, 52.64 mmol) and triethylamine (22 mL, 157.02 mmol) in dichloromethane (100 mL) at 0⁰C. After addition, the resulting solution was stirred at room temperature for 22 hours. Water (10 mL) was added to quench the reaction and some saturated NaCl solution (~30 mL) was added. The organic phase was separated and washed with brine (3 x 100 mL), dried over Na₂SO₄, and concentrated. The residue was dried under high vacuum to afford the product as an oil in quantitative yield. ¹H-NMR (CDCl₃) 4.38-4.35 (m, 4 H, 2 CH₂), 3.76- 3.73 (m, 4 H, 2 CH₂), 3.67-3.62 (m, 12 H, 6 CH₂), 3.12 (s, 6 H, 2 CH₃).

References:

WO2009/54916,2009,A2 Location in patent:Page/Page column 49