2-[(E)-3-chloroprop-1-enyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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

Procedure: In a 4 mL vial were mixed (E)-2-(3-chloroprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.195 ml, 0.988 mmol) and potassium carbonate (273 mg, 1.975 mmol) in anhydrous acetonitrile (2 ml). Benzylmethylamine (0.166 ml, 1.284 mmol) was added to this mixture, and the reaction was stirred vigorously overnight at room temperature. The reaction was diluted with ethyl acetate and washed with water and brine. The organic layer was dried with sodium sulfate, decanted, and concentrated to provide the title compound. washed with water and brine The organic layer was dried with sodium sulfate decanted concentrated

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

Procedure: In a 4 mL vial were mixed (E)-2-(3-chloroprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.195 ml, 0.988 mmol) and potassium carbonate (273 mg, 1.975 mmol) in anhydrous acetonitrile (2 ml). Benzylmethylamine (0.166 ml, 1.284 mmol) was added to this mixture, and the reaction was stirred vigorously overnight at room temperature. The reaction was diluted with ethyl acetate and washed with water and brine. The organic layer was dried with sodium sulfate, decanted, and concentrated to provide the title compound. washed with water and brine The organic layer was dried with sodium sulfate decanted concentrated

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

Procedure: A solution of (E)-2-(3-chloroprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1 g, 4.94 mmol) in acetonitrile (10 mL) was treated with potassium carbonate (1.366 g, 9.88 mmol) and pyrrolidine (0.531 mL, 6.42 mmol). The suspension was stirred at ambient temperature for 20 hours. The reaction mixture was filtered and the filtrate was concentrated on a rotary evaporator to provide the title compound. MS ESI(+) m/z 238.2 [M+H]+. The reaction mixture was filtered the filtrate was concentrated on a rotary evaporator

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

Procedure: A solution of (E)-2-(3-chloroprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1 g, 4.94 mmol) in acetonitrile (10 mL) was treated with potassium carbonate (1.366 g, 9.88 mmol) and pyrrolidine (0.531 mL, 6.42 mmol). The suspension was stirred at ambient temperature for 20 hours. The reaction mixture was filtered and the filtrate was concentrated on a rotary evaporator to provide the title compound. MS ESI(+) m/z 238.2 [M+H]+. The reaction mixture was filtered the filtrate was concentrated on a rotary evaporator

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

Procedure: A solution of (E)-3-chloroprop-1-enylboronic acid (5 g, 41 mmol), pinacol (4.9 g, 41 mmol), and magnesium sulfate (15 g, 120 mmol) in methylene chloride (100 mL) was stirred at room temperature for 18 h. The reaction mixture was filtered through silica gel and the filter cake was washed with methylene chloride. The filtrate was concentrated to afford the desired product (4.8 g, 60%) as a colorless oil: ESI MS m/z 203 [C9H16BClO2+H]+. The reaction mixture was filtered through silica gel the filter cake was washed with methylene chloride The filtrate was concentrated