tetradec-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: trans-2-Tetradecen-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 8.0 g (38 mmole) of 2-tetradecyn-1-ol in 30 ml of ether and 16 ml (55 mmole) of Red-Al in 40 ml of ether. Kugelrohr distillation afforded 7.67 g of clear oil. 1H NMR δ 5.66 (m, 2), 4.08 (d, 2, J=5 Hz) 2.03 (dd, 2, J=6, 13 Hz), 1.60 (br, 1), 1.4-1.2 (m, 18), 0.88 (t, 3, J=7 Hz). Kugelrohr distillation

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

Procedure: cis-2-Tetradecen-1-ol was prepared as described above for cis-2-decen-1-ol except that 1.0 g of 2-tetradecyn-1-ol, 50 mg of catalyst, and 0.10 ml of quinoline was used. A clear oil, 0.72 g, was obtained after kugelrohr distillation. 1H NMR δ 5.57 (m, 2) 4.19 9d, 2, J=6 Hz), 2.07 (dd, 2, J=6, 13 Hz), 1.5-1.2 (m, 18), 0.88 (t, 3, J=7 Hz). A clear oil, 0.72 g, was obtained after kugelrohr distillation

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

Procedure: 2-Tetradecyn-1-ol was prepared as described above for 2-dodecyn-1-ol except that 5.0 g (27 mmole) of 1-tridecyne in 200 ml of ether, 11.6 ml (29 mmole) of n-BuLi, and 874 mg (29 mmole) of paraformaldehyde was used. The reaction afforded a white solid after workup which was crystallized from petroleum ether to yield 4.78 g of white crystals, mp 44-6° C. 1H NMR δ 4.25 (m, 2), 2.20 (m, 2), 1.6-1.2 (m, 20), 0.88 (t, 3, J=7 Hz). The reaction afforded a white solid after workup which was crystallized from petroleum ether

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

Procedure: trans-2-Tetradecen-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 8.0 g (38 mmole) of 2-tetradecyn-1-ol in 30 ml of ether and 16 ml (55 mmole) of Red-Al in 40 ml of ether. Kugelrohr distillation afforded 7.67 g of clear oil. 1H NMR δ5.66 (m, 2), 4.08 (d, 2, J=5 Hz) 2.03 (dd, 2, J=6, 13 Hz), 1.60 (br, 1), 1.4-1.2 (m, 18), 0.88 (t, 3, J=7 HZ). Kugelrohr distillation

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

Procedure: cis-2-Tetradecen-1-ol was prepared as described above for cis-2-decen-1-ol except that 1.0 g of 2-tetradecyn-1-ol, 50 mg of catalyst, and 0.10 ml of quinoline was used. A clear oil, 0.72 g, was obtained after kugelrohr distillation. 1H NMR δ5.57 (m, 2) 4.19 9d, 2, J=6 Hz), 2.07 (dd, 2, J=6, 13 Hz), 1.5-1.2 (m, 18), 0.88 (t, 3, J=7 Hz). A clear oil, 0.72 g, was obtained after kugelrohr distillation

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

Procedure: 2-Tetradecyn-1-ol was prepared as described above for 2-dodecyn-1-ol except that 5.0 g (27 mmole) of 1-tridecyne in 200 ml of ether, 11.6 ml (29 mmole) of n-BuLi, and 874 mg (29 mmole) of paraformaldehyde was used. The reaction afforded a white solid after workup which was crystallized from petroleum ether to yield 4.78 g of white crystals, mp 44°-6° C. 1H NMR δ4.25 (m, 2), 2.20 (m, 2), 1.6-1.2 (m, 20), 0.88 (t, 3, J=7 Hz). The reaction afforded a white solid after workup which was crystallized from petroleum ether