octadec-9-enyl methanesulfonate

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

Procedure: To a mixture of 250 ml. of dichloromethane, 25 g. 1-hydroxyoctadec-9-ene and 16.7 g. of triethylamine cooled in an ice-salt bath to -10° C. is added dropwise, over 15 minutes, 18.9 g. of methanesulfonyl chloride. The mixture is cooled at -10° C. to -15° C. for 30 minutes and then washed with 300 ml. each of cold water, 10% hydrochloric acid, sodium carbonate solution and with saturated sodium chloride solution. The organic layer is dried with magnesium sulfate and concentrated in vacuo to give a pale yellow oil. To a mixture of 250 ml is added dropwise, over 15 minutes The mixture is cooled at -10° C. to -15° C. for 30 minutes washed with 300 ml The organic layer is dried with magnesium sulfate concentrated in vacuo to give a pale yellow oil

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

Procedure: A mixture of (2,3-bis-octadec-9-enyloxypropyl)-dimethylamine 4 (378 mg, 0.61 mmol) (synthesised from octadec-9-enyl mesylate and 3-dimethylamino-1,2-propanediol as described previously by Hurley et al., J. Org. Chem., 2004, 69, 980-984) and 3 (335 mg, 1.07 mmol) in acetone (5 ml) was stirred in a sealed-tube at 80° C. for 48 h. After cooling, the solvent was evaporated in vacuo. Purification by flash chromatography on silica (gradient; 5% to 10% methanol in dichloromethane) gave ME42 as an orange oil (140 mg, 27%). After cooling the solvent was evaporated in vacuo Purification by flash chromatography on silica (gradient; 5% to 10% methanol in dichloromethane)

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

Procedure: A mixture of (2,3-bis-octadec-9-enyloxypropyl)-dimethylamine 4 (378 mg, 0.61 mmol) (synthesised from octadec-9-enyl mesylate and 3-dimethylamino-1,2-propanediol as described previously by Hurley et al., J. Org. Chem., 2004, 69, 980-984) and 3 (335 mg, 1.07 mmol) in acetone (5 ml) was stirred in a sealed-tube at 80° C. for 48 h. After cooling, the solvent was evaporated in vacuo. Purification by flash chromatography on silica (gradient; 5% to 10% methanol in dichloromethane) gave ME42 as an orange oil (140 mg, 27%). After cooling the solvent was evaporated in vacuo Purification by flash chromatography on silica (gradient; 5% to 10% methanol in dichloromethane)

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

Procedure: To a mixture of 250 ml. of dichloromethane, 25 g. 1-hydroxyoctadec-9-ene and 16.7 g. of triethylamine cooled in an ice-salt bath to -10° C. is added dropwise, over 15 minutes, 18.9 g. of methanesulfonyl chloride. The mixture is cooled at -10° C. to -15° C. for 30 minutes and then washed with 300 ml. each of cold water, 10% hydrochloric acid, sodium carbonate solution and with saturated sodium chloride solution. The organic layer is dried with magnesium sulfate and concentrated in vacuo to give a pale yellow oil. To a mixture of 250 ml is added dropwise, over 15 minutes The mixture is cooled at -10° C. to -15° C. for 30 minutes washed with 300 ml The organic layer is dried with magnesium sulfate concentrated in vacuo to give a pale yellow oil

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

Procedure: To a mixture of 250 ml. of dichloromethane, 25 g. 1-hydroxyoctadec-9-ene and 16.7 g. of triethylamine cooled in an ice-salt bath to -10° C. is added dropwise, over 15 minutes, 18.9 g. of methanesulfonyl chloride. The mixture is cooled at -10° C. to -15° C. for 30 minutes and then washed with 300 ml. each of cold water, 10% hydrochloric acid, sodium carbonate solution and with saturated sodium chloride solution. The organic layer is dried with magnesium sulfate and concentrated in vacuo to give a pale yellow oil. To a mixture of 250 ml is added dropwise, over 15 minutes The mixture is cooled at -10° C. to -15° C. for 30 minutes washed with 300 ml The organic layer is dried with magnesium sulfate concentrated in vacuo to give a pale yellow oil

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

Procedure: A mixture of (2,3-bis-octadec-9-enyloxypropyl)-dimethylamine 4 (378 mg, 0.61 mmol) (synthesised from octadec-9-enyl mesylate and 3-dimethylamino-1,2-propanediol as described previously by Hurley et al., J. Org. Chem., 2004, 69, 980-984) and 3 (335 mg, 1.07 mmol) in acetone (5 ml) was stirred in a sealed-tube at 80° C. for 48 h. After cooling, the solvent was evaporated in vacuo. Purification by flash chromatography on silica (gradient; 5% to 10% methanol in dichloromethane) gave ME42 as an orange oil (140 mg, 27%). After cooling the solvent was evaporated in vacuo Purification by flash chromatography on silica (gradient; 5% to 10% methanol in dichloromethane)

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

Procedure: To a mixture of 250 ml. of dichloromethane, 25 g. 1-hydroxyoctadec-9-ene and 16.7 g. of triethylamine cooled in an ice-salt bath to -10° C. is added dropwise, over 15 minutes, 18.9 g. of methanesulfonyl chloride. The mixture is cooled at -10° C. to -15° C. for 30 minutes and then washed with 300 ml. each of cold water, 10% hydrochloric acid, sodium carbonate solution and with saturated sodium chloride solution. The organic layer is dried with magnesium sulfate and concentrated in vacuo to give a pale yellow oil. To a mixture of 250 ml is added dropwise, over 15 minutes The mixture is cooled at -10° C. to -15° C. for 30 minutes washed with 300 ml The organic layer is dried with magnesium sulfate concentrated in vacuo to give a pale yellow oil