4,4,5,5-Tetramethyl-2-[(Z)-1-(3-methylphenoxy)hex-1-en-2-yl]-1,3,2-dioxaborolane

Abstract

The title compound was previously prepared by Cui et al. (2013), and its derivatives were synthesized by Yang & Cheng (2001) and Whelligan et al. (2010). We present here the crystal structure of the compound (Fig. 1). In the molecule, the conformation of the dioxaborolane ring is similar to half chair, and the butyl group adopts an extended conformation with a C10-C11-C12-C13 torsion angle = 179.52 (19) . No hydrogen bonding is observed in the crystal. Synthesis and crystallizationTo a solution of 1-(hex-1-yn-1-yloxy)-3-methylbenzene (94 mg, 0.5 mmol) in 2.0 ml of tetrahydrofuran (THF) was added neat 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (HBpin) (71 mg, 0.55 mmol) under nitrogen atmosphere. After stirring at room temperature for 1.5 h, the reaction mixture was concentrated and purified by on silica gel (petroleum ether/EtOAc = 60/1).