trimethyl-[2-(2-methylphenyl)ethynyl]silane

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium hydroxide (10 g, 1.8 mol) added in 4 portions to a stirred solution of trimethyl-(2-methylphenyl)ethynylsilane (114.0 g, 0.61 mol) in methanol (400 ml) at 0° C. The mixture was stirred at 0° C. until the reaction was complete (by tlc 1:1 ethyl acetate:hexane). The mixture was neutralised by the addition of 10% hydrochloric acid and the product was extracted into dichloromethane (2×150 ml). The combined extracts were dried (MgSO4) and evaporated in vacuo. The residual oil was purified by short path distillation (Kugelrohr) to give 1-ethynyl-2-methylbenzene (52.03 g) as a clear oil. B.pt. 45° C./12 mBar. 250 MHz 1H-NMR (CDCl3) δ (ppm): 2.35 (s, 3H) (ArCH3), 3.2 (s, 1H)(CH), 7.0-7.2 (m, 3H) (3×ArH), 7.4 (m, 1H) (ArH); GC purity 98%, GC retention time 7.94 min. the product was extracted into dichloromethane (2×150 ml) The combined extracts were dried (MgSO4) evaporated in vacuo The residual oil was purified by short path distillation (Kugelrohr)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium hydroxide (10 g, 1.8 mol) added in 4 portions to a stirred solution of trimethyl-(2-methylphenyl)ethynylsilane (114.0 g, 0.61 mol) in methanol (400 ml) at 0° C. The mixture was stirred at 0° C. until the reaction was complete (by tlc 1:1 ethyl acetate:hexane). The mixture was neutralised by the addition of 10% hydrochloric acid and the product was extracted into dichloromethane (2×150 ml). The combined extracts were dried (MgSO4) and evaporated in vacuo. The residual oil was purified by short path distillation (Kugelrohr) to give 1-ethynyl-2-methylbenzene (52.03 g) as a clear oil. B.pt. 45° C./12 mBar. 250 MHz 1H-NMR (CDCl3) δ (ppm): 2.35 (s, 3H) (ArCH3), 3.2 (s, 1H)(CH), 7.0-7.2 (m, 3H) (3×ArH), 7.4 (m, 1H) (ArH); GC purity 98%, GC retention time 7.94 min. the product was extracted into dichloromethane (2×150 ml) The combined extracts were dried (MgSO4) evaporated in vacuo The residual oil was purified by short path distillation (Kugelrohr)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Iodotoluene (81.5 ml, 0.64 mol) and trimethylsilylacetylene (99 ml, 0.71 mol) were dissolved in triethylamine (250 ml). Triphenylphosphine (0.427 g, 1.6 mmol), copper (I) iodide (0.3 g, 1.6 mmol) and bistriphenyphosphinepalladium (II) dichloride (0.53 g, 0.71 mmol) were added and the mixture was heated under reflux for 18 h. The mixture was cooled to ambient temperature and carefully added to 10% hydrochloric acid (480 ml) and the product was extracted into hexane (3×200 ml). The extracts were washed with 10% hydrochloric acid (200 ml) and water (2×200 ml) then dried (MgSO4) and evaporated in vacuo to give trimethyl-(2-methylphenyl)ethynylsilane (114.06 g) as a yellow oil, which was used without further purification. the mixture was heated under reflux for 18 h the product was extracted into hexane (3×200 ml) The extracts were washed with 10% hydrochloric acid (200 ml) and water (2×200 ml) then dried (MgSO4) evaporated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Iodotoluene (81.5 ml, 0.64 mol) and trimethylsilylacetylene (99 ml, 0.71 mol) were dissolved in triethylamine (250 ml). Triphenylphosphine (0.427 g, 1.6 mmol), copper (I) iodide (0.3 g, 1.6 mmol) and bistriphenyphosphinepalladium (II) dichloride (0.53 g, 0.71 mmol) were added and the mixture was heated under reflux for 18 h. The mixture was cooled to ambient temperature and carefully added to 10% hydrochloric acid (480 ml) and the product was extracted into hexane (3×200 ml). The extracts were washed with 10% hydrochloric acid (200 ml) and water (2×200 ml) then dried (MgSO4) and evaporated in vacuo to give trimethyl-(2-methylphenyl)ethynylsilane (114.06 g) as a yellow oil, which was used without further purification. the mixture was heated under reflux for 18 h the product was extracted into hexane (3×200 ml) The extracts were washed with 10% hydrochloric acid (200 ml) and water (2×200 ml) then dried (MgSO4) evaporated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium hydroxide (10 g, 1.8 mol) added in 4 portions to a stirred solution of trimethyl-(2-methylphenyl)ethynylsilane (114.0 g, 0.61 mol) in methanol (400 ml) at 0° C. The mixture was stirred at 0° C. until the reaction was complete (by tlc 1:1 ethyl acetate:hexane). The mixture was neutralised by the addition of 10% hydrochloric acid and the product was extracted into dichloromethane (2×150 ml). The combined extracts were dried (MgSO4) and evaporated in vacuo. The residual oil was purified by short path distillation (Kugelrohr) to give 1-ethynyl-2-methylbenzene (52.03 g) as a clear oil. B.pt. 45° C./12 mBar. 250 MHz 1H-NMR (CDCl3) δ (ppm): 2.35 (s, 3H) (ArCH3), 3.2 (s, 1H)(CH), 7.0-7.2 (m, 3H) (3×ArH), 7.4 (m, 1H) (ArH); GC purity 98%, GC retention time 7.94 min. the product was extracted into dichloromethane (2×150 ml) The combined extracts were dried (MgSO4) evaporated in vacuo The residual oil was purified by short path distillation (Kugelrohr)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Iodotoluene (81.5 ml, 0.64 mol) and trimethylsilylacetylene (99 ml, 0.71 mol) were dissolved in triethylamine (250 ml). Triphenylphosphine (0.427 g, 1.6 mmol), copper (I) iodide (0.3 g, 1.6 mmol) and bistriphenyphosphinepalladium (II) dichloride (0.53 g, 0.71 mmol) were added and the mixture was heated under reflux for 18 h. The mixture was cooled to ambient temperature and carefully added to 10% hydrochloric acid (480 ml) and the product was extracted into hexane (3×200 ml). The extracts were washed with 10% hydrochloric acid (200 ml) and water (2×200 ml) then dried (MgSO4) and evaporated in vacuo to give trimethyl-(2-methylphenyl)ethynylsilane (114.06 g) as a yellow oil, which was used without further purification. the mixture was heated under reflux for 18 h the product was extracted into hexane (3×200 ml) The extracts were washed with 10% hydrochloric acid (200 ml) and water (2×200 ml) then dried (MgSO4) evaporated in vacuo