oct-3-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:

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:0.00; pressure:0.00; stir:

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

Procedure: Hydrogen gas was blown into a solution prepared by dissolving 126 g of 3-octyn-1-ol in 100 ml of n-hexane with admixture of 10 g of a Lindlar catalyst and 10 g of pyridine and the introduction of hydrogen was continued for about 4 hours when absorption of hydrogen had ceased. Removal of solid matter from the reaction mixture by filtration and stripping of n-hexane gave cis-3-octen-1-ol, which was dissolved in a mixture of 250 g of methylene chloride and 111 g of triethylamine. prepared when absorption of hydrogen Removal of solid matter from the reaction mixture by filtration and stripping of n-hexane

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

Procedure: The hydrogen reduction of this 3-octyn-1-ol is carried out by dissolving the compound in n-hexane with addition of 3 to 20% by weight of a Lindlar catalyst and introducing hydrogen at room temperature with agitation (reaction (iii)). Removal of the catalyst by filtration and n-hexane by distillation from the reaction mixture gives cis-3-octen-1-ol in an almost quantitative yield. Removal of the catalyst by filtration and n-hexane by distillation from the reaction mixture

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

Procedure: Into the solution of the Grignard reagent obtained above and kept at 0° to 60° C., ethylene oxide is added dropwise preferably in an amount of 1.6 to 3 times by moles based on the starting butylacetylene and the reaction mixture is hydrolyzed by contacting with an aqueous acidic solution followed by distillation to give 3-octyn-1-ol (reaction (ii)). The yield is usually 80 to 85% of the theoretical value. kept at 0° to 60° C. followed by distillation

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

Procedure: Into the solution of the Grignard reagent obtained above and kept at 0° to 60° C., ethylene oxide is added dropwise preferably in an amount of 1.6 to 3 times by moles based on the starting butylacetylene and the reaction mixture is hydrolyzed by contacting with an aqueous acidic solution followed by distillation to give 3-octyn-1-ol (reaction (ii)). The yield is usually 80 to 85% of the theoretical value. kept at 0° to 60° C. followed by distillation

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

Procedure: Triphenylphosphonium dibromide (36.8 g, 87.2 mmol) was suspended in diethyl ether at -20° C. and a solution of 3-octyne-1-ol (10.0 g, 79.2 mmol) was added dropwise over a twenty minute period. The mixture was allowed to stir overnight. The mixture was poured into ice-water and solids precipitated which were collected by filtration. The organic layer was separated, washed with 1N aqueous sodium hydroxide, water and dried over magnesium sulfate. The organic layer was then filtered and concentrated in vacuo to give a residue which was taken up in hexanes, filtered to remove undissolved material and concentrated to give 1-bromo-3-octyne as an orange oil (14.2 g, 96%). 1H NMR (300 MHZ) spectral data were consistent with the desired bromide (plus a trace of triphenylphosphine), and the crude product was used directly in the next step. precipitated which were collected by filtration The organic layer was separated washed with 1N aqueous sodium hydroxide, water dried over magnesium sulfate The organic layer was then filtered concentrated in vacuo to give a residue which filtered to remove undissolved material concentrated