3-hydroxy-3-methylbutyl methanesulfonate synthesis

Yield:135859-47-1 72%

Reaction Conditions:

with triethylamine in dichloromethane at 20; for 7.5 h;Cooling with ice;

Steps:

4.1.1.72. 3-Hydroxy-3-methylbutyl methanesulfonate

3-Methyl-1,3-butandiol (3.83 g, 36.8 mmol) was dissolved in CH₂Cl₂ (150 ml). Triethylamine (6.66 ml, 47.8 mmol) and methanesulfonyl chloride (3.13 ml, 40.5 mmol) were added to the ice-cooled solution, and stirred for 7.5 h at room temperature. Water (100 ml) was added, and the organic layer was separated. The aqueous layer was extracted with CH₂Cl₂. Then, combined organic layer was washed with brine, and dried over Na₂SO₄. The solvent was removed in a reduced presser to give title compound (4.79 g, 26.3 mmol, 72%) as colorless oil. ¹H NMR (CDCl₃) δ 1.30 (6H, s), 1.96 (2H, t, J = 6.8 Hz), 3.02 (3H, s), 4.42 (2H, t, J = 6.8 Hz)

References:

Ichikawa, Masanori;Yokomizo, Aki;Itoh, Masao;Haginoya, Noriyasu;Sugita, Kazuyuki;Usui, Hiroyuki;Terayama, Koji;Kanda, Akira [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 17,p. 5207 - 5224] Location in patent:experimental part