Pentane → HCID 66747024, compound

Participants

Reaction Conditions

Reaction Steps

At 0° C. under an atmosphere of argon, granular lithium (1.30 g, 187 mmol) was suspended in Et2O (60 ml), and a solution of bromocyclopropane (10.7 g, 88.5 mmol) in Et2O (60 ml) was added during 30 min. dropwise. After stirring 30 min. at 0° C., the resulting solution was added during 60 min. dropwise at this temp. to a solution of tetrachlorosilane (5.00 g, 27.0 mmol) in Et2O (120 ml), and stirring was continued for 7 h at room temp. In a separate vessel under an atmosphere of argon, a 1.6 M solution of tert-butyl lithium in pentane (18.4 ml, 29.4 mmol) was added during 30 min. dropwise with stirring at −78° C. to a solution of ethyl vinyl ether (2.12 g, 29.4 mmol) in THF (22 ml). This reaction mixture was then allowed to warm to 0° C. within 3 h, prior to being cooled to −50° C. and added dropwise with stirring during 10 min. at −50° C. to the first reaction mixture. After stirring for 16 h at room temp., the mixture was poured into water (200 ml), and stirring was continued for 10 min. The organic layer was separated, and the aqueous one extracted with Et2O (2×75 ml). The combined organic solutions were dried (Na2SO4), and concentrated in a rotary evaporator to afford crude tricyclopropyl(1-ethoxyvinyl)silane, which was taken up in acetone/1 N HCl (2:1, 72 ml). The reaction mixture was stirred for 45 min. prior to the addition of water/Et2O (1:1, 100 ml). The organic layer was separated, and the aqueous one extracted with Et2O (2×50 ml). The combined ethereal extracts were dried (Na2SO4) and concentrated under reduced pressure. Silica-gel chromatography (silica gel 40-63 μm, hexane/EtOAc, 9:1, relevant fractions were determined by GC) of the resulting residue provided 2.58 g (49% over 2 steps) of acetyl(tricyclopropyl)silane.

Provenance & Evidence