non-8-yn-1-ol

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

Procedure: The same procedure for 8-nonyn-1-ol was followed with 2- pentadecyn-1-ol (4.51 g, 20.1 mmol), KH (2.38 g, 59.4 mmol), and 1,3-diaminopropane (65 mL). This produced 3.18 g of white solid (70%): mp 42-44° C. IR (thin film( ν 3430, 2926, 2252 cm−1: 1H—NMR δ4.30 (t, 1H, J=5.0 Hz), 3.64 (t, 2H, J=6.6 Hz), 2.18 (td, 2H, J=2.6 Hz, 6.6 Hz), 1.94 (t, 1H, J=2.6 Hz), 1.49-1.26 (bm, 22H); 13C—NMR δ 84.8, 68.0, 63.1, 32.8, 29.6, (2C), 29.5 (2C), 29.4, 28.9, 28.5, 28.7, 28.0, 25.7, 18.4; MS m/z 231.53 (M++Li). Anal. Calcd for C15H28O: C, 80.29; H, 12.58. Found: C, 18.20; H, 12.50.

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

Procedure: The same procedure for 8-nonyn-1-ol was followed with 9-dodecyn-1-ol (4.68 g, 25.7 mmol), KH(3.09 g, 77.0 mmol), and 1,3-diaminopropane (70 mL). This produced 4.33 g of yellow oil (93%): IR (neat) ν 3317,2930, 2121 cm−1; 1H—NMR δ 3.62 (t, 2H, J=6.6 Hz), 2.17 (td, 2H, J=2.6 Hz, 7.1 Hz), 1.93 (t, 1H, J=2.6 Hz), 1.76 (bs, 1H), 1.55 (m, 4H), 1.28 bm, 12H); 13C—NMR δ 84.8, 68.0, 63.0, 32.7, 29.5, 29.4 (2C), 29.0, 28.7, 28.4, 25.7, 18.4; MS m/z 189.18 (M++Li).

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

Procedure: The same procedure for 8-nonyn-1-ol was followed with 3-octyn-1-ol (6.89 g, 54.6 mmol), KH (6.57 g, 16.4 mmol), and 1,3-diaminopropane (60 mL). This produced 6.09 g of clear yellowish liquid (88%): IR (neat)ν 3360, 2896, 2116 cm−1; 1H—NMR δ 3.44 (t, 2H, J=6.6 Hz), 3.27 (bs, 1H), 2.04 (td, 2H, J=2.6 Hz, 6.6 Hz), 1.83 (t, 1H, J=2.6 Hz), 1.39 (m, 4H), 1.25 (m, 4H); 13C NMR δ 84.5, 68.3, 62.2, 32.3, 28.3, 25.2, (2C), 18.2; MS m/z 136.00 (m++Li). Anal. Calcd for C8H14O: C, 76.14; H, 11.18. Found: C, 76.04; H, 11.16.

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

Procedure: In a round-bottom flask equipped with a stir bar and under an atmosphere of argon was added KH (4.46 g, 111 mmol). The flask was cooled to 0° C. and 1,3-diaminopropane (50 mL) was added slowly via syringe. The solution was stirred for 45 min. Then 2-nonyn-1-ol, dissolved in of 1,3-diaminopropane (30 mL), was added dropwise via syringe to the stirring solution. The reaction was stirred for an additional 30 min at 0° C. before warming to room temperature overnight. The reaction was again cooled to 0° C. before quenching with water. The compound was extracted with Et2O, washed with HCL, water, and brine, dried with MgSO4, and concentrated. This produced 4.94 g of dark orange oil which was purified by flash column chromatography on silica gel (2.5% Et2O in hexane to 50% Et2O in hexane) to give 3.21 g of clear oil (67%): IR (near) ν 3409, 2931, 2242 cm−1, 1H—NMR δ 3.59 (t, 2H, J=7.0 Hz), 2.14 (td, 2H, J=3.0 Hz, 7.0 Hz), 2.10 (s, 1H), 1.91 (t, 1H, J=3.0 Hz), 1.50 (bm, 4H), 1.30 (bm, 6H); 13C—NMR δ 84.6, 68.1, 62.8, 32.6, 28.8, 28.6, 28.3, 25.6, 18.3; MS m/z 147.10 (M++Li). Anal. Calcd for C9H16O: C, 77.09; H, 11.46. Found: C, 77.00; H, 11.46. In a round-bottom flask equipped with a stir bar and under an atmosphere of argon was added KH (4.46 g, 111 mmol) was added dropwise via syringe to the stirring solution The reaction was stirred for an additional 30 min at 0° C. before warming to room temperature overnight The reaction was again cooled to 0° C. before quenching with water The compound was extracted with Et2O washed with HCL, water, and brine dried with MgSO4 concentrated This produced 4.94 g of dark orange oil which was purified by flash column chromatography on silica gel (2.5% Et2O in hexane to 50% Et2O in hexane)

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

Procedure: The same procedure for 8-nonyn-1-ol was followed with 2- pentadecyn-1-ol (4.51 g, 20.1 mmol), KH (2.38 g, 59.4 mmol), and 1,3-diaminopropane (65 mL). This produced 3.18 g of white solid (70%): mp 42-44° C. IR (thin film( ν 3430, 2926, 2252 cm−1: 1H—NMR δ4.30 (t, 1H, J=5.0 Hz), 3.64 (t, 2H, J=6.6 Hz), 2.18 (td, 2H, J=2.6 Hz, 6.6 Hz), 1.94 (t, 1H, J=2.6 Hz), 1.49-1.26 (bm, 22H); 13C—NMR δ 84.8, 68.0, 63.1, 32.8, 29.6, (2C), 29.5 (2C), 29.4, 28.9, 28.5, 28.7, 28.0, 25.7, 18.4; MS m/z 231.53 (M++Li). Anal. Calcd for C15H28O: C, 80.29; H, 12.58. Found: C, 18.20; H, 12.50.

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

Procedure: The same procedure for 8-nonyn-1-ol was followed with 2- pentadecyn-1-ol (4.51 g, 20.1 mmol), KH (2.38 g, 59.4 mmol), and 1,3-diaminopropane (65 mL). This produced 3.18 g of white solid (70%): mp 42-44° C. IR (thin film( ν 3430, 2926, 2252 cm−1: 1H—NMR δ4.30 (t, 1H, J=5.0 Hz), 3.64 (t, 2H, J=6.6 Hz), 2.18 (td, 2H, J=2.6 Hz, 6.6 Hz), 1.94 (t, 1H, J=2.6 Hz), 1.49-1.26 (bm, 22H); 13C—NMR δ 84.8, 68.0, 63.1, 32.8, 29.6, (2C), 29.5 (2C), 29.4, 28.9, 28.5, 28.7, 28.0, 25.7, 18.4; MS m/z 231.53 (M++Li). Anal. Calcd for C15H28O: C, 80.29; H, 12.58. Found: C, 18.20; H, 12.50.

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

Procedure: The same procedure for 8-nonyn-1-ol was followed with 9-dodecyn-1-ol (4.68 g, 25.7 mmol), KH(3.09 g, 77.0 mmol), and 1,3-diaminopropane (70 mL). This produced 4.33 g of yellow oil (93%): IR (neat) ν 3317,2930, 2121 cm−1; 1H—NMR δ 3.62 (t, 2H, J=6.6 Hz), 2.17 (td, 2H, J=2.6 Hz, 7.1 Hz), 1.93 (t, 1H, J=2.6 Hz), 1.76 (bs, 1H), 1.55 (m, 4H), 1.28 bm, 12H); 13C—NMR δ 84.8, 68.0, 63.0, 32.7, 29.5, 29.4 (2C), 29.0, 28.7, 28.4, 25.7, 18.4; MS m/z 189.18 (M++Li).

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

Procedure: The same procedure for 8-nonyn-1-ol was followed with 9-dodecyn-1-ol (4.68 g, 25.7 mmol), KH(3.09 g, 77.0 mmol), and 1,3-diaminopropane (70 mL). This produced 4.33 g of yellow oil (93%): IR (neat) ν 3317,2930, 2121 cm−1; 1H—NMR δ 3.62 (t, 2H, J=6.6 Hz), 2.17 (td, 2H, J=2.6 Hz, 7.1 Hz), 1.93 (t, 1H, J=2.6 Hz), 1.76 (bs, 1H), 1.55 (m, 4H), 1.28 bm, 12H); 13C—NMR δ 84.8, 68.0, 63.0, 32.7, 29.5, 29.4 (2C), 29.0, 28.7, 28.4, 25.7, 18.4; MS m/z 189.18 (M++Li).

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

Procedure: The same procedure for 8-nonyn-1-ol was followed with 3-octyn-1-ol (6.89 g, 54.6 mmol), KH (6.57 g, 16.4 mmol), and 1,3-diaminopropane (60 mL). This produced 6.09 g of clear yellowish liquid (88%): IR (neat)ν 3360, 2896, 2116 cm−1; 1H—NMR δ 3.44 (t, 2H, J=6.6 Hz), 3.27 (bs, 1H), 2.04 (td, 2H, J=2.6 Hz, 6.6 Hz), 1.83 (t, 1H, J=2.6 Hz), 1.39 (m, 4H), 1.25 (m, 4H); 13C NMR δ 84.5, 68.3, 62.2, 32.3, 28.3, 25.2, (2C), 18.2; MS m/z 136.00 (m++Li). Anal. Calcd for C8H14O: C, 76.14; H, 11.18. Found: C, 76.04; H, 11.16.

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

Procedure: In a round-bottom flask equipped with a stir bar and under an atmosphere of argon was added KH (4.46 g, 111 mmol). The flask was cooled to 0° C. and 1,3-diaminopropane (50 mL) was added slowly via syringe. The solution was stirred for 45 min. Then 2-nonyn-1-ol, dissolved in of 1,3-diaminopropane (30 mL), was added dropwise via syringe to the stirring solution. The reaction was stirred for an additional 30 min at 0° C. before warming to room temperature overnight. The reaction was again cooled to 0° C. before quenching with water. The compound was extracted with Et2O, washed with HCL, water, and brine, dried with MgSO4, and concentrated. This produced 4.94 g of dark orange oil which was purified by flash column chromatography on silica gel (2.5% Et2O in hexane to 50% Et2O in hexane) to give 3.21 g of clear oil (67%): IR (near) ν 3409, 2931, 2242 cm−1, 1H—NMR δ 3.59 (t, 2H, J=7.0 Hz), 2.14 (td, 2H, J=3.0 Hz, 7.0 Hz), 2.10 (s, 1H), 1.91 (t, 1H, J=3.0 Hz), 1.50 (bm, 4H), 1.30 (bm, 6H); 13C—NMR δ 84.6, 68.1, 62.8, 32.6, 28.8, 28.6, 28.3, 25.6, 18.3; MS m/z 147.10 (M++Li). Anal. Calcd for C9H16O: C, 77.09; H, 11.46. Found: C, 77.00; H, 11.46. In a round-bottom flask equipped with a stir bar and under an atmosphere of argon was added KH (4.46 g, 111 mmol) was added dropwise via syringe to the stirring solution The reaction was stirred for an additional 30 min at 0° C. before warming to room temperature overnight The reaction was again cooled to 0° C. before quenching with water The compound was extracted with Et2O washed with HCL, water, and brine dried with MgSO4 concentrated This produced 4.94 g of dark orange oil which was purified by flash column chromatography on silica gel (2.5% Et2O in hexane to 50% Et2O in hexane)

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

Procedure: The same procedure for 8-nonyn-1-ol was followed with 2- pentadecyn-1-ol (4.51 g, 20.1 mmol), KH (2.38 g, 59.4 mmol), and 1,3-diaminopropane (65 mL). This produced 3.18 g of white solid (70%): mp 42-44° C. IR (thin film( ν 3430, 2926, 2252 cm−1: 1H—NMR δ4.30 (t, 1H, J=5.0 Hz), 3.64 (t, 2H, J=6.6 Hz), 2.18 (td, 2H, J=2.6 Hz, 6.6 Hz), 1.94 (t, 1H, J=2.6 Hz), 1.49-1.26 (bm, 22H); 13C—NMR δ 84.8, 68.0, 63.1, 32.8, 29.6, (2C), 29.5 (2C), 29.4, 28.9, 28.5, 28.7, 28.0, 25.7, 18.4; MS m/z 231.53 (M++Li). Anal. Calcd for C15H28O: C, 80.29; H, 12.58. Found: C, 18.20; H, 12.50.

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

Procedure: The same procedure for 8-nonyn-1-ol was followed with 9-dodecyn-1-ol (4.68 g, 25.7 mmol), KH(3.09 g, 77.0 mmol), and 1,3-diaminopropane (70 mL). This produced 4.33 g of yellow oil (93%): IR (neat) ν 3317,2930, 2121 cm−1; 1H—NMR δ 3.62 (t, 2H, J=6.6 Hz), 2.17 (td, 2H, J=2.6 Hz, 7.1 Hz), 1.93 (t, 1H, J=2.6 Hz), 1.76 (bs, 1H), 1.55 (m, 4H), 1.28 bm, 12H); 13C—NMR δ 84.8, 68.0, 63.0, 32.7, 29.5, 29.4 (2C), 29.0, 28.7, 28.4, 25.7, 18.4; MS m/z 189.18 (M++Li).