Boron trifluoride etherate → HCID 131727263, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-(1,1-dimethylethyl)dimethylsilyloxynona-1,8-diyne (1.80 g, 10 mmol) in THF (10 mL) is stirred at −78° C. while a solution of n-butyllithium (2.0M in hexanes, 4.95 mL) is added. The mixture is stirred for ten minutes at −78 degrees C. and boron trifluoride etherate (9.9 mmol, 1.25 mL) is added. After another thirty minutes stirring at −78° C., a solution of 5-formyl-octahydro-5′-(1-methoxymethoxy undecyl)-[2.2′]-bifuran (1.35 g, 3.5 mmol) in THF (8 mL) is added. The resulting solution is stirred at −78° C. for four hours, and is poured into an aqueous solution of NH4Cl (100 mL, 2.0 M). The mixture is extracted with ethyl acetate (3×100 mL) and the combined organic fractions are washed (1× water), filtered, (saturated aqueous NaCl, sodium sulfate) and concentrated. Chromatography (hexane-2:1 hexane:ethyl acetate gradient over silica gel 230-400 mesh) affords 5-(1,1-dimethylethyl)dimethylsilyloxy-10-methoxymethoxy-10-[octahydro-5′-(1-hydroxyundecyl) [2.2′-bifuran]-5-yl]deca-1,8-diyne as an oil.

Provenance & Evidence