(E)-oct-3-en-1-ol

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

Procedure: A solution of oct-3-yn-1-ol (2.52 g, 20.0 mmol), t-BuOH (5 g), THF (10 mL) and liquid NH3 was cooled to −36° C. Pieces of Lithium (0.34 g, 50 mmol) were introduced with vigorous stirrng and maintaining the temperature. After 2 h, NH3 was allowed to evaporate overnight. Saturated NH4Cl solution was added and the reaction mixture was extracted with hexane. The combined organic layers were washed with 1 M HCl, aqueous NaHCO3 and brine successively and dried. Evaporation of the solvent gave trans-oct-3-en-1-ol (2.44 g, 95%) as a pale yellow oil, which was used in the next step without further purification: 1H NMR (300 MHz, CDCl3) δ 5.54 (1H, m), 5.36 (1H, m), 3.66 (2H, t, J=6.3 Hz), 2.25 (2H, m), 2.02 (2H, m), 1.74 (1H, br s), 1.31 (4H, m), 0.88 (3H, t, J=7.2 Hz); 13C NMR (75 MHz, CDCl3) δ 134.27, 125.78, 62.22, 36.22, 32.59, 31.86, 22.47, 14.20. maintaining the temperature to evaporate overnight Saturated NH4Cl solution was added the reaction mixture was extracted with hexane The combined organic layers were washed with 1 M HCl, aqueous NaHCO3 and brine successively dried Evaporation of the solvent

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

Procedure: To a solution of trans-oct-3-en-1-ol (1.28 g, 10.0 mmol) in DMF (25 mL) was added triphenylphosphine (2.92 g, 11.1 mmol). The solution was cooled to 0° C. and NBS (1.92 g, 10.8 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (1 mL). The solution was diluted with ether (100 mL), washed with water, saturated aqueous NaHCO3 and brine successively. The organic layer was dried and concentrated. The residue was purified by flash chromatography on silica gel, eluting with hexane to afford trans-1-bromo-oct-3-ene (1.40 g, 73%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 5.54 (1H, m), 5.39 (1H, m), 3.37 (2H, t, J=7.2 Hz), 2.54 (2H, m), 2.02 (2H, m) 1.34 (4H, m), 0.89 (3H, t, J=7.2 Hz); 13C NMR (75 MHz, CDCl3) δ 134.09, 126.45, 36.34, 33.21, 32.48, 31.73, 22.45, 14.24. the reaction was quenched with methanol (1 mL) The solution was diluted with ether (100 mL) washed with water, saturated aqueous NaHCO3 and brine successively The organic layer was dried concentrated The residue was purified by flash chromatography on silica gel eluting with hexane

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

Procedure: A solution of oct-3-yn-1-ol (2.52 g, 20.0 mmol), t-BuOH (5 g), THF (10 mL) and liquid NH3 was cooled to −36° C. Pieces of Lithium (0.34 g, 50 mmol) were introduced with vigorous stirrng and maintaining the temperature. After 2 h, NH3 was allowed to evaporate overnight. Saturated NH4Cl solution was added and the reaction mixture was extracted with hexane. The combined organic layers were washed with 1 M HCl, aqueous NaHCO3 and brine successively and dried. Evaporation of the solvent gave trans-oct-3-en-1-ol (2.44 g, 95%) as a pale yellow oil, which was used in the next step without further purification: 1H NMR (300 MHz, CDCl3) δ 5.54 (1H, m), 5.36 (1H, m), 3.66 (2H, t, J=6.3 Hz), 2.25 (2H, m), 2.02 (2H, m), 1.74 (1H, br s), 1.31 (4H, m), 0.88 (3H, t, J=7.2 Hz); 13C NMR (75 MHz, CDCl3) δ 134.27, 125.78, 62.22, 36.22, 32.59, 31.86, 22.47, 14.20. maintaining the temperature to evaporate overnight Saturated NH4Cl solution was added the reaction mixture was extracted with hexane The combined organic layers were washed with 1 M HCl, aqueous NaHCO3 and brine successively dried Evaporation of the solvent

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

Procedure: To a solution of trans-oct-3-en-1-ol (1.28 g, 10.0 mmol) in DMF (25 mL) was added triphenylphosphine (2.92 g, 11.1 mmol). The solution was cooled to 0° C. and NBS (1.92 g, 10.8 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (1 mL). The solution was diluted with ether (100 mL), washed with water, saturated aqueous NaHCO3 and brine successively. The organic layer was dried and concentrated. The residue was purified by flash chromatography on silica gel, eluting with hexane to afford trans-1-bromo-oct-3-ene (1.40 g, 73%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 5.54 (1H, m), 5.39 (1H, m), 3.37 (2H, t, J=7.2 Hz), 2.54 (2H, m), 2.02 (2H, m) 1.34 (4H, m), 0.89 (3H, t, J=7.2 Hz); 13C NMR (75 MHz, CDCl3) δ 134.09, 126.45, 36.34, 33.21, 32.48, 31.73, 22.45, 14.24. the reaction was quenched with methanol (1 mL) The solution was diluted with ether (100 mL) washed with water, saturated aqueous NaHCO3 and brine successively The organic layer was dried concentrated The residue was purified by flash chromatography on silica gel eluting with hexane

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

Procedure: A solution of oct-3-yn-1-ol (2.52 g, 20.0 mmol), t-BuOH (5 g), THF (10 mL) and liquid NH3 was cooled to −36° C. Pieces of Lithium (0.34 g, 50 mmol) were introduced with vigorous stirrng and maintaining the temperature. After 2 h, NH3 was allowed to evaporate overnight. Saturated NH4Cl solution was added and the reaction mixture was extracted with hexane. The combined organic layers were washed with 1 M HCl, aqueous NaHCO3 and brine successively and dried. Evaporation of the solvent gave trans-oct-3-en-1-ol (2.44 g, 95%) as a pale yellow oil, which was used in the next step without further purification: 1H NMR (300 MHz, CDCl3) δ 5.54 (1H, m), 5.36 (1H, m), 3.66 (2H, t, J=6.3 Hz), 2.25 (2H, m), 2.02 (2H, m), 1.74 (1H, br s), 1.31 (4H, m), 0.88 (3H, t, J=7.2 Hz); 13C NMR (75 MHz, CDCl3) δ 134.27, 125.78, 62.22, 36.22, 32.59, 31.86, 22.47, 14.20. maintaining the temperature to evaporate overnight Saturated NH4Cl solution was added the reaction mixture was extracted with hexane The combined organic layers were washed with 1 M HCl, aqueous NaHCO3 and brine successively dried Evaporation of the solvent

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

Procedure: A mixture of Ph3P (3.205 g, 12.2 mmol), imidazole (1.221 g, 17.9 mmol), and I2 (3.024 g, 11.9 mmol) in CH2Cl2 (38 mL) was stirred at room temperature. After 15 min., a solution of 7-2 (1.283 g, 10.0 mmol) in CH2Cl2 (4.8 mL) was added by cannula, rinsing with 4 mL CH2Cl2. After 3 h, the mixture was filtered through basic alumina, washing with 10% ethyl acetate/hexanes. The filtrate was evaporated and the residue was purified by flash chromatography on silica gel (Isco Combiflash unit) to provide the title compound (2.323 g, 98%). rinsing with 4 mL CH2Cl2 After 3 h the mixture was filtered through basic alumina washing with 10% ethyl acetate/hexanes The filtrate was evaporated the residue was purified by flash chromatography on silica gel (Isco Combiflash unit)

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

Procedure: LiAlH4 (13.5 mL, 13.5 mmol, 1 M/THF) was added to an ice cold solution of (E)-oct-3-enoic acid (7-1, 1.86 g, 13.1 mmol) in THF (48 mL). The reaction was allowed to warm to room temperature and after 2 h, was cooled in an ice bath and 50 mL H2O was added slowly. NaOH (3 M, 50 mL) and H2O (50 mL) were added and the resulting mixture was extracted with dichloromethane (3×100 mL). The combined organic layer was washed with brine (100 mL) and was then dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (Isco Combiflash unit) gave the title compound (1.283 g, 76%). was cooled in an ice bath the resulting mixture was extracted with dichloromethane (3×100 mL) The combined organic layer was washed with brine (100 mL) was then dried (Na2SO4) filtered evaporated Purification of the residue by flash chromatography on silica gel (Isco Combiflash unit)

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

Procedure: To a solution of trans-oct-3-en-1-ol (1.28 g, 10.0 mmol) in DMF (25 mL) was added triphenylphosphine (2.92 g, 11.1 mmol). The solution was cooled to 0° C. and NBS (1.92 g, 10.8 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (1 mL). The solution was diluted with ether (100 mL), washed with water, saturated aqueous NaHCO3 and brine successively. The organic layer was dried and concentrated. The residue was purified by flash chromatography on silica gel, eluting with hexane to afford trans-1-bromo-oct-3-ene (1.40 g, 73%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 5.54 (1H, m), 5.39 (1H, m), 3.37 (2H, t, J=7.2 Hz), 2.54 (2H, m), 2.02 (2H, m) 1.34 (4H, m), 0.89 (3H, t, J=7.2 Hz); 13C NMR (75 MHz, CDCl3) δ 134.09, 126.45, 36.34, 33.21, 32.48, 31.73, 22.45, 14.24. the reaction was quenched with methanol (1 mL) The solution was diluted with ether (100 mL) washed with water, saturated aqueous NaHCO3 and brine successively The organic layer was dried concentrated The residue was purified by flash chromatography on silica gel eluting with hexane