Dimethyl(3,3,4,4,5,5,6,6,6-nonafluorohexyl)chlorosilane → HCID 86663261, compound

Participants

Reaction Conditions

Reaction Steps

In an oven-dried 250-mL round bottom flask, 3,3,4,4,5,5,6,6,6-nonafluorohexyldimethylchlorosilane (4.58 g, 13.4 mmol) was dissolved in anhydrous THF (10 mL) and cooled in an ice bath. Ethynylmagnesium bromide (34 mL, 17 mmol, 0.5 M in THF) was added slowly, then the mixture was heated to 60° C. for 12 hr. The reaction was quenched with water and dilute sulfuric acid (i.e., a 10 wt % solution of the sulfuric acid (95-98%) in water) to dissolve the salts, then hexane was added and the organic layer was separated. The organic layer was washed with water (5×20 mL), dried over magnesium sulfate, filtered, and concentrated under vacuum to yield the crude product. Purification using chromatography on silica gel with hexane as an eluant yielded a colorless liquid (3.52 g, 10.6 mmol, 80%). Analysis of the colorless product provided the following data: 1H-NMR (200 MHz, CDCl3) δ=2.4 (s, 1H), 2.1 (m, 2H), 0.8 (m, 2H), 0.2 (s, 6H).

Provenance & Evidence