1-Octyne, 8-broMo-

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

Procedure: cis-13-Octadecen-2-yn-1-ol was synthesized in the following manner. Thus, 153 g (0.81 mole) of 8-bromo-1-octyne were added dropwise at 50° to 55° C. to 1 mole of methyl magnesium chloride dissolved in 300 ml of tetrahydrofuran and the mixture was agitated for 1 hour followed by the addition of 2 g of dilithium tetrachlorocuprate Li2CuCl4. Thereafter, a solution of 1 mole of cis-4-nonenyl magnesium chloride dissolved in 300 ml of tetrahydrofuran was added dropwise to the reaction mixture at 40° to 55° C. and the mixture was agitated for 4 hours at 48° C. was added dropwise to the reaction mixture at 40° to 55° C. the mixture was agitated for 4 hours at 48° C.

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

Procedure: cis-13-Octadecen-2-yn-1-ol was synthesized in the following manner. Thus, 153 g (0.81 mole) of 8-bromo-1-octyne were added dropwise at 50° to 55° C. to 1 mole of methyl magnesium chloride dissolved in 300 ml of tetrahydrofuran and the mixture was agitated for 1 hour followed by the addition of 2 g of dilithium tetrachlorocuprate Li2CuCl4. Thereafter, a solution of 1 mole of cis-4-nonenyl magnesium chloride dissolved in 300 ml of tetrahydrofuran was added dropwise to the reaction mixture at 40° to 55° C. and the mixture was agitated for 4 hours at 48° C. was added dropwise to the reaction mixture at 40° to 55° C. the mixture was agitated for 4 hours at 48° C.

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: cis-13-Octadecen-3-yn-2-ol was synthesized in the following manner. Thus, a Grignard mixture containing 1.0 mole of methyl magnesium chloride dissolved in 300 ml of tetrahydrofuran was added dropwise into 153 g (0.81 mole) of 8-bromo-1-octyne kept at 50° to 55° C. and the reaction mixture was agitated for 1 hour at 60° C. followed by the addition of 2 g of copper (I) iodide CuI. Thereafter, a second Grignard mixture containing 1.0 mole of cis-3-octenyl magnesium chloride dissolved in 300 ml of tetrahydrofuran was added dropwise to the reaction mixture kept at 40° to 55° C. and the reaction mixture was agitated for 4 hours at 40° C. kept at 50° to 55° C. was added dropwise to the reaction mixture kept at 40° to 55° C. the reaction mixture was agitated for 4 hours at 40° C.

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

Procedure: 8-Bromo-1-octyne (2.0 g, 10.6 mmol) prepared in step 1) was added to a dehydrated dimethylformamide (25 mL) solution containing 6-(thien-2-yl)-2-amino purine (1.2 g, 5.5 mmol) and potassium carbonate (2.3 g, 16.5 mmol), followed by stirring at room temperature for 15 hours. The reaction solution was concentrated and was separated between ethyl acetate and water. The organic layer was washed with saturated brine, was dried over anhydrous sodium sulfate, and was purified by medium-pressure preparative column chromatography to yield 6-(thien-2-yl)-9-(7-octynyl)-2-amino purine (1.6 g, 4.9 mmol, 87%). The reaction solution was concentrated was separated between ethyl acetate and water The organic layer was washed with saturated brine was dried over anhydrous sodium sulfate was purified by medium-pressure preparative column chromatography

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

Procedure: 8-Bromo-1-octyne (2.0 g, 10.6 mmol) prepared in step 1) was added to a dehydrated dimethylformamide (25 mL) solution containing 6-(thien-2-yl)-2-amino purine (1.2 g, 5.5 mmol) and potassium carbonate (2.3 g, 16.5 mmol), followed by stirring at room temperature for 15 hours. The reaction solution was concentrated and was separated between ethyl acetate and water. The organic layer was washed with saturated brine, was dried over anhydrous sodium sulfate, and was purified by medium-pressure preparative column chromatography to yield 6-(thien-2-yl)-9-(7-octynyl)-2-amino purine (1.6 g, 4.9 mmol, 87%). The reaction solution was concentrated was separated between ethyl acetate and water The organic layer was washed with saturated brine was dried over anhydrous sodium sulfate was purified by medium-pressure preparative column chromatography

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

Procedure: Dehydrated dichloromethane (20 mL) and triphenylphosphine (5.91 g, 22.5 mmol) were added to 8-hydroxy-1-octyne (1.95 g, 15 mmol). The mixture was cooled to 0° C. and was then dropwise added to dehydrated dichloromethane (10 mL) containing carbon tetrabromide (7.46 g, 22.5 mmol), followed by stirring at room temperature for 2 hours. After separation between dichloromethane (100 mL) and 5% sodium bicarbonate (150 mL), the organic layer was washed with saturated brine (150 mL). The organic layer was dried over sodium sulfate and then concentrated. The concentrated product was purified by silica gel column chromatography (dichloromethane:methanol=from 100:0 to 99:1) to yield 8-bromo-1-octyne (crude). After separation between dichloromethane (100 mL) and 5% sodium bicarbonate (150 mL) the organic layer was washed with saturated brine (150 mL) The organic layer was dried over sodium sulfate concentrated The concentrated product was purified by silica gel column chromatography (dichloromethane:methanol=from 100:0 to 99:1)

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

Procedure: cis-13-Octadecen-2-yn-1-ol was synthesized in the following manner. Thus, 153 g (0.81 mole) of 8-bromo-1-octyne were added dropwise at 50° to 55° C. to 1 mole of methyl magnesium chloride dissolved in 300 ml of tetrahydrofuran and the mixture was agitated for 1 hour followed by the addition of 2 g of dilithium tetrachlorocuprate Li2CuCl4. Thereafter, a solution of 1 mole of cis-4-nonenyl magnesium chloride dissolved in 300 ml of tetrahydrofuran was added dropwise to the reaction mixture at 40° to 55° C. and the mixture was agitated for 4 hours at 48° C. was added dropwise to the reaction mixture at 40° to 55° C. the mixture was agitated for 4 hours at 48° C.

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: cis-13-Octadecen-3-yn-2-ol was synthesized in the following manner. Thus, a Grignard mixture containing 1.0 mole of methyl magnesium chloride dissolved in 300 ml of tetrahydrofuran was added dropwise into 153 g (0.81 mole) of 8-bromo-1-octyne kept at 50° to 55° C. and the reaction mixture was agitated for 1 hour at 60° C. followed by the addition of 2 g of copper (I) iodide CuI. Thereafter, a second Grignard mixture containing 1.0 mole of cis-3-octenyl magnesium chloride dissolved in 300 ml of tetrahydrofuran was added dropwise to the reaction mixture kept at 40° to 55° C. and the reaction mixture was agitated for 4 hours at 40° C. kept at 50° to 55° C. was added dropwise to the reaction mixture kept at 40° to 55° C. the reaction mixture was agitated for 4 hours at 40° C.

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

Procedure: 8-Bromo-1-octyne (2.0 g, 10.6 mmol) prepared in step 1) was added to a dehydrated dimethylformamide (25 mL) solution containing 6-(thien-2-yl)-2-amino purine (1.2 g, 5.5 mmol) and potassium carbonate (2.3 g, 16.5 mmol), followed by stirring at room temperature for 15 hours. The reaction solution was concentrated and was separated between ethyl acetate and water. The organic layer was washed with saturated brine, was dried over anhydrous sodium sulfate, and was purified by medium-pressure preparative column chromatography to yield 6-(thien-2-yl)-9-(7-octynyl)-2-amino purine (1.6 g, 4.9 mmol, 87%). The reaction solution was concentrated was separated between ethyl acetate and water The organic layer was washed with saturated brine was dried over anhydrous sodium sulfate was purified by medium-pressure preparative column chromatography

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

Procedure: Dehydrated dichloromethane (20 mL) and triphenylphosphine (5.91 g, 22.5 mmol) were added to 8-hydroxy-1-octyne (1.95 g, 15 mmol). The mixture was cooled to 0° C. and was then dropwise added to dehydrated dichloromethane (10 mL) containing carbon tetrabromide (7.46 g, 22.5 mmol), followed by stirring at room temperature for 2 hours. After separation between dichloromethane (100 mL) and 5% sodium bicarbonate (150 mL), the organic layer was washed with saturated brine (150 mL). The organic layer was dried over sodium sulfate and then concentrated. The concentrated product was purified by silica gel column chromatography (dichloromethane:methanol=from 100:0 to 99:1) to yield 8-bromo-1-octyne (crude). After separation between dichloromethane (100 mL) and 5% sodium bicarbonate (150 mL) the organic layer was washed with saturated brine (150 mL) The organic layer was dried over sodium sulfate concentrated The concentrated product was purified by silica gel column chromatography (dichloromethane:methanol=from 100:0 to 99:1)