Tetrahydrofuran → HCID 68161628, compound

Participants

Reaction Conditions

Reaction Steps

A solution of n-BuLi (14.1 mL, 1.6 M in hexanes, 22.5 mmol, 1.3 equivalents) was added dropwise to a solution of 2-hexyl-5-iodofuran (3.8 g, 17.4 mmol) in dry tetrahydrofuran (THF, 100 mL) at −78° C. under N2. The reaction mixture was allowed to reach to room temperature and stirred for 1 h. The resulting mixture was cooled to −78° C., Bu3SnCl (6.1 mL, 22.5 mmol) was added dropwise and the reaction mixture was allowed to reach room temperature and stirred for 2 h. The mixture was quenched with water, extracted with hexane, dried (MgSO4), and evaporated. Flash chromatography on a basified (NEt3) silica, using hexane as eluent gave Tributyl(5′-hexyl-[2,2′-bifuran]-5-yl)stannane) (1.9 g, 20% yield) as a colorless oil. 1H NMR (300 MHz, CDCl3): ppm. 13C NMR (75 MHz, CDCl3): δ 106.1, 155.9, 151.4, 145.7, 122.9, 106.4, 105.4, 104.0, 31.6, 28.9, 28.8, 28.1, 28.0, 27.2 22.6, 14.7, 14.1, 10.2 ppm. FIRMS (FD): m/z calcd for C26H44O2Sn: 508.2368. found 508.2374.

Provenance & Evidence