Tetrahydrofuran → HCID 22666345, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6-vinylbenzo[b]thiophene (2.124 g, 13.3 mmol) in 80 mL THF was added to a solution of 9-borabicyclo[3.3.1]nonane (9-BBN) (5.21 g, 21.3 mmol) in 80 mL THF, rinsing with 5 mL THF. The solution was heated at 60° C. for 2.5 h and then a solution of H2O2 (36 mL, 35%)/NaOH (36 mL. 0.5 M)/H2O (9 mL) was added slowly. The reaction was then heated to 85° C. for 1 h, cooled to room temperature and 50 mL H2O was added. The mixture was extracted with ethyl acetate (3×50 mL), the combined organic solution was washed with brine and then was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (ethyl acetate/hexanes) gave the title compound (2.338 g, 99%).

Provenance & Evidence