13465-73-1 → HCID 86663269, compound

Participants

Reaction Conditions

Reaction Steps

In an oven dried round bottom flask, (3,3,4,4,5,5,5-heptafluoropentyl)diisopropylsilane (10 g, 32 mmol) was dissolved in allyl bromide (20 mL) and the flask was flushed with N2. PdCl2 (40 mg) was added and the solution was heated to 60° C. for 12 hr. Solvent was removed on a rotary evaporator to yield a brown suspension that was taken up in pentane and filtered. Solvent removal yielded the bromosilane as a brown liquid (12.1 g). The bromosilane, (3,3,4,4,5,5,5-heptafluoropentyldiisopropylsilyl)bromide, was treated with ethynylmagnesium bromide (70 mL, 35 mmol, 0.5 M in THF) in anhydrous THF (20 mL) and heated to 40° C. for 4 hr. After cooling, the reaction was quenched by the slow addition of water (20 mL) and dilute sulfuric acid sufficient to dissolve the magnesium salts. Pentane was added and the organic layer was separated. The aqueous layer was extracted with pentane an additional time, then the organic layers were combined, washed with water (5×10 mL) and brine, dried over MgSO4, and filtered. Solvent was removed and the crude product was taken up in hexane and rinsed through a thin pad of silica. Solvent removal yielded the product as a colorless liquid (9.7 g, 29 mmol, 90%). Analysis of the product provided the following data: 1H-NMR (400 MHz, CDCl3) δ=2.4 (s, 1H), 2.2 (m, 2H), 1.0 (m, 14H), 0.8 (m, 2H).

Provenance & Evidence