(Z)-1-bromooctadec-9-ene

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: This example illustrates a synthesis of 1-(9,10-Oxidoctadecyl)-3,7-dimethylxanthine (inventive compound no. 2541). Triphenylphosphine (5.24 g; 20 mmol) was added in portions to a solution of oleyl alcohol (5.37 g; 20 mmol) and carbontetrabromide (6.63 g; 20 mmol) in 400 mL of dichloromethane and stirred for an hour at room temperature. The solvent was removed under reduced pressure and the residue extracted with hexane (3×200 mL). Further purification was done by flash chromatography over silica gel using hexane as eluant to yield 5.82 g (88% yield) of 1-bromo-9-octadecene. The solvent was removed under reduced pressure the residue extracted with hexane (3×200 mL) Further purification

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

Procedure: This example illustrates a synthesis of 1-(9,10-Oxidoctadecyl)-3,7-dimethylxanthine (inventive compound no. 2541). Triphenylphosphine (5.24 g; 20 mmol) was added in portions to a solution of oleyl alcohol (5.37 g; 20 mmol) and carbontetrabromide (6.63 g; 20 mmol) in 400 mL of dichloromethane and stirred for an hour at room temperature. The solvent was removed under reduced pressure and the residue extracted with hexane (3×200 mL). Further purification was done by flash chromatography over silica gel using hexane as eluant to yield 5.82 g (88% yield) of 1-bromo-9-octadecene. The solvent was removed under reduced pressure the residue extracted with hexane (3×200 mL) Further purification

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

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

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

Procedure: Sodium hydride (95%, 84 mg, 3.5 mmol) was added to a solution of theobromine (0.595 g, 3.2 mmol) in dimethylsulfoxide (15 ml). After 20 minutes of stirring, 1-bromo-9-octadecene (0.995 g, 3 mmol), prepared above, was added. After 6 hours of stirring at room temperature, the reaction mixture was warmed to 60° C. over 3 hours and then poured into a separatory funnel containing 50 ml of water. The reaction mixture was extracted with five 40 ml aliquots of dichloromethane. The organic extracts were combined, washed with water (50 ml) and brine (50 ml) and dried over anhydrous magnesium sulfate. Removing the solvent under reduced pressure resulted in a crude product further purified by flash chromatography over silica gel using a 30% acetone/petroleum ether eluant, yielding 0.44 g of 1-(9-octadecenyl)-3,7-dimethylxanthine (34 % yield). was added After 6 hours of stirring at room temperature poured into a separatory funnel The reaction mixture was extracted with five 40 ml aliquots of dichloromethane washed with water (50 ml) and brine (50 ml) dried over anhydrous magnesium sulfate Removing the solvent under reduced pressure resulted in a crude product further purified by flash chromatography over silica gel using a 30% acetone/petroleum ether eluant

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

Procedure: This example is a method of synthesis for inventive compound no. 3508. Triphenylphosphine (5.24 g, 20 mmol) was added incrementally to a solution of oleyl alcohol (5.37 g, 20 mmol) and carbontetrabromide (6.63 g, 20 mmol) in 400 ml of dichloromethane, the resulting reaction mixture being stirred for an hour at room temperature. Removing the solvent under reduced pressure, left a residue, which was extracted with three 200 ml aliquots of hexane. Further purification by flash chromatography over silica gel using a hexane eluant produced 5.82 g of 1-bromo-9-octadecene (88% yield). a method of synthesis for inventive compound no the resulting reaction mixture Removing the solvent under reduced pressure left a residue, which was extracted with three 200 ml aliquots of hexane Further purification by flash chromatography over silica gel using a hexane eluant

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

Procedure: This example is a method of synthesis for inventive compound no. 3508. Triphenylphosphine (5.24 g, 20 mmol) was added incrementally to a solution of oleyl alcohol (5.37 g, 20 mmol) and carbontetrabromide (6.63 g, 20 mmol) in 400 ml of dichloromethane, the resulting reaction mixture being stirred for an hour at room temperature. Removing the solvent under reduced pressure, left a residue, which was extracted with three 200 ml aliquots of hexane. Further purification by flash chromatography over silica gel using a hexane eluant produced 5.82 g of 1-bromo-9-octadecene (88% yield). a method of synthesis for inventive compound no the resulting reaction mixture Removing the solvent under reduced pressure left a residue, which was extracted with three 200 ml aliquots of hexane Further purification by flash chromatography over silica gel using a hexane eluant

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

Procedure: This example is a method of synthesis for inventive compound no. 3508. Triphenylphosphine (5.24 g, 20 mmol) was added incrementally to a solution of oleyl alcohol (5.37 g, 20 mmol) and carbontetrabromide (6.63 g, 20 mmol) in 400 ml of dichloromethane, the resulting reaction mixture being stirred for an hour at room temperature. Removing the solvent under reduced pressure, left a residue, which was extracted with three 200 ml aliquots of hexane. Further purification by flash chromatography over silica gel using a hexane eluant produced 5.82 g of 1-bromo-9-octadecene (88% yield). a method of synthesis for inventive compound no the resulting reaction mixture Removing the solvent under reduced pressure left a residue, which was extracted with three 200 ml aliquots of hexane Further purification by flash chromatography over silica gel using a hexane eluant

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

Procedure: This example illustrates a synthesis of 1-(9,10-Oxidoctadecyl)-3,7-dimethylxanthine (inventive compound no. 2541). Triphenylphosphine (5.24 g; 20 mmol) was added in portions to a solution of oleyl alcohol (5.37 g; 20 mmol) and carbontetrabromide (6.63 g; 20 mmol) in 400 mL of dichloromethane and stirred for an hour at room temperature. The solvent was removed under reduced pressure and the residue extracted with hexane (3×200 mL). Further purification was done by flash chromatography over silica gel using hexane as eluant to yield 5.82 g (88% yield) of 1-bromo-9-octadecene. The solvent was removed under reduced pressure the residue extracted with hexane (3×200 mL) Further purification

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

Procedure: Sodium hydride (95%, 84 mg, 3.5 mmol) was added to a solution of theobromine (0.595 g, 3.2 mmol) in dimethylsulfoxide (15 ml). After 20 minutes of stirring, 1-bromo-9-octadecene (0.995 g, 3 mmol), prepared above, was added. After 6 hours of stirring at room temperature, the reaction mixture was warmed to 60° C. over 3 hours and then poured into a separatory funnel containing 50 ml of water. The reaction mixture was extracted with five 40 ml aliquots of dichloromethane. The organic extracts were combined, washed with water (50 ml) and brine (50 ml) and dried over anhydrous magnesium sulfate. Removing the solvent under reduced pressure resulted in a crude product further purified by flash chromatography over silica gel using a 30% acetone/petroleum ether eluant, yielding 0.44 g of 1-(9-octadecenyl)-3,7-dimethylxanthine (34% yield). was added After 6 hours of stirring at room temperature poured into a separatory funnel The reaction mixture was extracted with five 40 ml aliquots of dichloromethane washed with water (50 ml) and brine (50 ml) dried over anhydrous magnesium sulfate Removing the solvent under reduced pressure resulted in a crude product further purified by flash chromatography over silica gel using a 30% acetone/petroleum ether eluant