dec-2-yn-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To 60 ml. anhydrous ether and 1.5 g. 7-cyclopropylheptanoyl chloride is added 1.2 g. 2-decyn-1-ol. The mixture is cooled to 0° and 0.8 ml. pyridine is added. The solution is stirred at room temperature for 1 day. The product is worked up using the procedure of Example 1C to yield 2-decynyl 7-cyclopropylheptanoate. The mixture is cooled to 0°

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

Procedure: To 60 ml. anhydrous ether and 1.5 g. 7-cyclopropylheptanoyl chloride is added 1.2 g. 2-decyn-1-ol. The mixture is cooled to 0° and 0.8 ml. pyridine is added. The solution is stirred at room temperature for 1 day. The product is worked up using the procedure of Example 1C to yield 2-decynyl 7-cyclopropylheptanoate. The mixture is cooled to 0°

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: trans-2-Decen-1-ol was prepared by reduction of the propargyl alcohol by the method described by Jones and Denmark (Org. Syn., 1985, 64, 182-8) using 15 g (97 mmole) of 2-decyn-1-ol in 40 ml of ether and 48 ml (162 mmole) of Red-Al (sodium bis(2-methoxyethoxy)aluminum hybride) in 50 ml of ether. Kugelrohr distillation afforded 11.59 g of a clear oil. 1H NMR δ 5.66 (m, 2), 4.07 (d, 2, J=5 Hz), 20.3 (dd, 2, J=6, 13 hz), 1.68 (br, 1), 1.4-1.2 (m, 10), 0.88 (t, 3, J=7 Hz). Kugelrohr distillation

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

Procedure: To a solution of 10.0 g of 2-decyn-1-ol in 150 ml of petroleum ether was added 500 mg of Pd on CaCO3 poisoned with lead (Lindlar catalyst). Quinoline (2.0 ml) was then added to this mixture and the flask was evacuated (house vacuum, ca. 50 mm Hg) and flushed with H2 three times and left under a H2 atmosphere. The mixture was stirred vigorously until uptake of H2 was no longer evident and TLC (SiO2 /20% ether:pet. ether) showed no starting material. The catalyst was removed by filtration through a 4 cm pad of celite and the filtrate was washed two times with 100 ml of 1 N HCl, once with 100 ml of saturated NaHCO3, once with 100 ml of brine, dried over MgSO4, filtered and the solvent evaporated to give a pale yellow oil. Kugelrohr distillation (100-120° C. oven, 0.2 mm) affords 8.81 g of clear oil. 1H NMR δ 5.57 (m,2), 4.20 (t, 2, J=5 Hz), 2.07 (dd, 2, J=6, 12 Hz), 1.5-1.1 (m, 10), 0.88 (t, 3, J=7 Hz). the flask was evacuated (house vacuum, ca. 50 mm Hg) flushed with H2 three times left under a H2 atmosphere The catalyst was removed by filtration through a 4 cm pad of celite the filtrate was washed two times with 100 ml of 1 N HCl once with 100 ml of saturated NaHCO3, once with 100 ml of brine, dried over MgSO4 filtered the solvent evaporated to give a pale yellow oil Kugelrohr distillation (100-120° C. oven, 0.2 mm)

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

Procedure: To a solution of 3.85 g. of 2-decyn-1-ol and 3.95 g. of pyridine in 100 ml. ether is added 3.0 g. of cyclopropanecarboxylic acid chloride. The mixture is stirred overnight under nitrogen. The reaction mixture is poured into distilled water, washed with dilute hydrochloric acid and then with sodium bicarbonate and solvent removed to yield 2-decynyl cyclopropanecarboxylate, b.p. 96°-97° (bath) at 0.1 mm. The reaction mixture is poured into distilled water washed with dilute hydrochloric acid with sodium bicarbonate and solvent removed

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

Procedure: trans-2-Decen-1-ol was prepared by reduction of the propargyl alcohol by the method described by Jones and Denmark (Org. Syn., 1985, 64, 182-8) using 15 g (97 mmole) of 2-decyn-1-ol in 40 ml of ether and 48 ml (162 mmole) of Red-Al (sodium bis(2-methoxyethoxy)aluminum hybride) in 50 ml of ether. Kugelrohr distillation afforded 11.59 g of a clear oil. 1H NMR δ5.66 (m, 2), 4.07 (d, 2, J=5 Hz), 20.3 (dd, 2, J=6, 13 hz), 1.68 (br, 1), 1.4-1.2 (m, 10), 0.88 (t, 3, J=7 Hz). Kugelrohr distillation

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

Procedure: To a solution of 10.0 g of 2-decyn-1-ol in 150 ml petroleum ether was added 500 mg of Pd on CaCO3 poisoned with lead (Lindlar catalyst). Quinoline (2.0 ml) was then added to this mixture and the flask was evacuated (house vacuum, ca. 50 mm Hg) and flushed with H2 three times and left under a H2 atmosphere. The mixture was stirred vigorously until uptake of H2 was no longer evident and TLC (SiO2 /20% ether:pet. ether) showed no starting material. The catalyst was removed by filtration through a 4 cm pad of celite and the filtrate was washed two times with 100 ml of 1N HCl, once with 100 ml of saturated NaHCO3, once with 100 ml of brine, dried over MgSO4, filtered and the solvent evaporated to give a pale yellow oil. Kugelrohr distillation (100°-120° C. oven, 0.2 mm) affords 8.81 g of clear oil. 1H NMR δ 5.57 (m,2), 4.20 (t, 2, J=5 Hz), 2.07 (dd, 2, J=6, 12 Hz), 1.5-1.1 (m, 10), 0.88 (t, 3, J=7 Hz). the flask was evacuated (house vacuum, ca. 50 mm Hg) flushed with H2 three times left under a H2 atmosphere The catalyst was removed by filtration through a 4 cm pad of celite the filtrate was washed two times with 100 ml of 1N HCl once with 100 ml of saturated NaHCO3, once with 100 ml of brine, dried over MgSO4 filtered the solvent evaporated to give a pale yellow oil Kugelrohr distillation (100°-120° C. oven, 0.2 mm)