Hexane → HCID 101372458, compound

Participants

Reaction Steps

An oven dried 500 mL round bottom flask with nitrogen atmosphere was charged with hexane (100 mL), tetrahydrofuran (20 mL), and trimethylsilylacetylene (4.8 g, 48.9 mmol) and cooled with an ice bath. N-butyllithium (2.5 M in hexane, 19.4 mL) was added dropwise and the reaction mixture was allowed to warm to room temperature. The reaction product (20.0 g) from the previously described step, “Synthesis of 3-(N-methylnonafluorobutanesulfonamido)propyl) diisopropylsilyl chloride,” was slowly added and the contents allowed to stir for sixteen hours. Water was added slowly (100 mL) and the mixture was stirred vigorously. The organic layer was separated, and the water layer extracted with 100 mL of hexane. The organic layers were combined and concentrated under reduced pressure to a brown oil. The oil was purified using chromatography on silica gel with hexane as an eluant, resulting in 23.9 g of the trimethylsilyl-protected acetylene as a clear oil. The oil (23.9 g, 42.2 mmol) was charged to an oven dried 500 mL round bottom flask. Methanol (50 mL), tetrahydrofuran (50 mL), and 5% aqueous NaOH (1 mL) were added to the flask and then stirred for one hour. Water (100 mL) was then added, and stirred vigorously. The organic layer was separated, and the aqueous layer was extracted two times with hexane (2×100 mL). The organic layers were combined and concentrated under reduced pressure to yield 3-(N-methylnonafluorobutanesulfonamido)propyl)diisopropylsilyl acetylene as a clear oil (11.2 g, 54%).

Provenance & Evidence