non-8-en-1-ol

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

Procedure: In a glovebox, a 20 mL vial was charged with 8-nonenol (0.58 g, 4.1 mmol), 1-pentene (4 mL), and THF (4 mL). A solution of 1 (0.026 g, 1 mol %) in THF (0.5 mL) was added, and the mixture was stirred in an open vial for 4 hours. The vial was removed from the glovebox, the reaction was quenched with excess ethyl vinyl ether, and the solvent was removed in vacuo. Flash chromatography of the residue (SiO2, using a gradient of hexanes to 20% EtOAc in hexanes) provided 12 (0.56 g, 73% yield, 86% Z as determined by 1H-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.36 (2H, m), 3.64 (2H, br t, J=5.3 Hz), 2.01 (4H, m), 1.36 (2H, m), 1.28-1.40 (11H, m), 0.90 (3H, t, J=7.4 Hz); 13C NMR (CDCl3): δ 130.0, 129.7, 63.1, 32.8, 29.3 (4C), 27.2, 25.7, 22.9, 13.8; HRMS (EI): 184.1805, [C12H24O]+ requires 184.1827. The vial was removed from the glovebox the reaction was quenched with excess ethyl vinyl ether the solvent was removed in vacuo

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

Procedure: In a glovebox, a 20 mL vial was charged with 8-nonenol (0.58 g, 4.1 mmol), 1-pentene (4 mL), and THF (4 mL). A solution of 1 (0.026 g, 1 mol %) in THF (0.5 mL) was added, and the mixture was stirred in an open vial for 4 hours. The vial was removed from the glovebox, the reaction was quenched with excess ethyl vinyl ether, and the solvent was removed in vacuo. Flash chromatography of the residue (SiO2, using a gradient of hexanes to 20% EtOAc in hexanes) provided 12 (0.56 g, 73% yield, 86% Z as determined by 1H-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.36 (2H, m), 3.64 (2H, br t, J=5.3 Hz), 2.01 (4H, m), 1.36 (2H, m), 1.28-1.40 (11H, m), 0.90 (3H, t, J=7.4 Hz); 13C NMR (CDCl3): δ 130.0, 129.7, 63.1, 32.8, 29.3 (4C), 27.2, 25.7, 22.9, 13.8; HRMS (EI): 184.1805, [C12H24O]+ requires 184.1827. The vial was removed from the glovebox the reaction was quenched with excess ethyl vinyl ether the solvent was removed in vacuo

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

Procedure: This example illustrates a synthesis procedure for 1-(8,9-dihydroxynonyl)-3,7-dimethylxanthine (CT1561). The synthesis began by adding a solution of 8-nonene-1-ol (1.50 g, 10.5 mmol) in dichloromethane (100 ml) at 0° C. to methanesulfonyl chloride (1.20 g, 813 μl, 10.5 mmol), followed by triethylamine (1.59 g, 15.8 mmol). After stirring for 1 hr at 0° C., the reaction mixture was allowed to warm to room temperature. The reaction mixture was poured into 100 ml of water and extracted with dichloromethane (3×50 ml). The organic portions were combined, dried with sodium sulfate, and evaporated to give 9-methanesulfonyl-1-nonene as a yellow oil (2.25 g, 97% yield, which was used without further purification. to warm to room temperature extracted with dichloromethane (3×50 ml) dried with sodium sulfate evaporated

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

Procedure: This example illustrates a synthesis procedure for 1-(8,9-dihydroxynonyl)-3,7-dimethylxanthine (CT1561). The synthesis began by adding a solution of 8-nonene-1-ol (1.50 g, 10.5 mmol) in dichloromethane (100 ml) at 0° C. to methanesulfonyl chloride (1.20 g, 813 μl, 10.5 mmol), followed by triethylamine (1.59 g, 15.8 mmol). After stirring for 1 hr at 0° C., the reaction mixture was allowed to warm to room temperature. The reaction mixture was poured into 100 ml of water and extracted with dichloromethane (3×50 ml). The organic portions were combined, dried with sodium sulfate, and evaporated to give 9-methanesulfonyl-1-nonene as a yellow oil (2.25 g, 97% yield, which was used without further purification. to warm to room temperature extracted with dichloromethane (3×50 ml) dried with sodium sulfate evaporated

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

Procedure: A solution of 0.064 mole of 8-nonen-1-ol and 0.19 mole of triethylamine (3 molar excess) in 100 mL of hexane was prepared. To the stirred solution, 0.13 mole of methanesulfonyl chloride (2 molar excess) was added dropwise over 5 min. After the addition was complete, stirring was continued for 2 h. Cold water was poured into the reaction mixture to destroy any excess methanesulfonyl chloride. The aqueous layer was separated from the organic layer, and was extracted with diethyl ether. The organic phases were combined and washed with dilute HC, H2O, 5% NaHCO3 and H2O. The organic layer was dried over MgSO4 and the solvent was removed by rotary evaporation. The respective reactions afforded 8-nonen-1-mesylate in 95% yield. The final product had the following properties: 1H NMR (300 MHZ, CDCl3): δ 5.86-5.72 (m, 1H), 5.02-4.91 (m, 2H), 4.23 (t, J=7.4 Hz, 2H), 2.97 (s, 2H), 2.05 (m, 2H), 1.80 (m, 2H), 1.39-1.27 (m, 8H). 13C NMR (75.5 MHZ, CDCl3): δ 138.33, 113.78, 69.85, 36.52, 33.19, 28.59, 28.35 (2 peaks), 28.23, 24.86. After the addition to destroy any excess methanesulfonyl chloride The aqueous layer was separated from the organic layer was extracted with diethyl ether washed with dilute HC, H2O, 5% NaHCO3 and H2O The organic layer was dried over MgSO4 the solvent was removed by rotary evaporation

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

Procedure: In a glovebox, a 20 mL vial was charged with 8-nonenol (0.58 g, 4.1 mmol), 1-pentene (4 mL), and THF (4 mL). A solution of 1 (0.026 g, 1 mol %) in THF (0.5 mL) was added, and the mixture was stirred in an open vial for 4 hours. The vial was removed from the glovebox, the reaction was quenched with excess ethyl vinyl ether, and the solvent was removed in vacuo. Flash chromatography of the residue (SiO2, using a gradient of hexanes to 20% EtOAc in hexanes) provided 12 (0.56 g, 73% yield, 86% Z as determined by 1H-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.36 (2H, m), 3.64 (2H, br t, J=5.3 Hz), 2.01 (4H, m), 1.36 (2H, m), 1.28-1.40 (11H, m), 0.90 (3H, t, J=7.4 Hz); 13C NMR (CDCl3): δ 130.0, 129.7, 63.1, 32.8, 29.3 (4C), 27.2, 25.7, 22.9, 13.8; HRMS (EI): 184.1805, [C12H24O]+ requires 184.1827. The vial was removed from the glovebox the reaction was quenched with excess ethyl vinyl ether the solvent was removed in vacuo