Sodium hydride → (1-(((tert-Butyldimethylsilyl)oxy)methyl)cyclopropyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added NaH (1.08 g, 27.0 mmol) and THF (35 mL). The reaction mixture was cooled to about 0° C. and a solution of cyclobutane-1,1-diyldimethanol (3.14 g, 27.0 mmol, prepared according to DE 19735574, Beispiel 8d) in THF (100 mL) was added dropwise. The reaction mixture was stirred for about 30 min and then a solution of tert-butylchlorodimethylsilane (4.07 g, 27.0 mmol) in THF (50 mL) was added dropwise. The reaction mixture was warmed to ambient temperature and the reaction mixture was stirred for about 1 h. The reaction mixture was quenched with the addition of saturated aqueous NaHCO3 (200 mL) and the mixture was extracted with EtOAc (3×200 mL). The organics were combined and washed with brine (500 mL), dried with Na2SO4, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel 120 g RediSep® column; heptane/EtOAc gradient from 1:0 to 0:1) to give the title compound (3.23 g, 52%). 1H NMR (CDCl3) δ 3.72 (s, 2H), 3.70 (s, 2H), 1.97-1.68 (m, 6H), 0.91 (s, 9H), 0.91 (s, 3H), 0.09 (s, 3H).

Provenance & Evidence