dec-9-en-1-ol

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

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

Procedure: Compound G was prepared from 9-decen-1-ol and 9-decenoic acid following the general procedure already discussed and shown in FIG. 12. Pure compound G was a colorless oil by column chromatography with Ethyl acetate/Hexane=1:50.

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

Procedure: Compound F was prepared from Oleoyl chloride and 9-decen-1-ol following the general procedure already discussed and shown in FIG. 11. Pure compound F was a colorless oil obtained by column chromatography with Ethyl acetate/Hexane=1:40.

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

Procedure: The reaction was performed in standard glassware under an atmosphere of N2. To 150 ml of diethylether were added 9.8 g (0.1 mol) propiolic acid ethyl ester, 15.6g (0.1 mol) dec-9-en-1-ol and 10.1 g (0.1 mol) N-methylmorpholine. This solution was kept without stirring at room temperature for 24 hours. The mixture was evaporated under vacuum and the residue purified by bulb to bulb distillation (bp: 85-90° C.; 0.006 mbar) to yield 23.2 g (916%) of an oil. The mixture was evaporated under vacuum the residue purified by bulb to bulb distillation (bp: 85-90° C.; 0.006 mbar)

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

Procedure: Starting Material: dec-9-en-1-ol and benzyl chloroformate.

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

Procedure: 9-Decen-1-ol (Rosalva) in the amount of 50.00 g (0.320 mol) and maleic anhydride in the amount of 12.55 g (0.128 mol), toluene in the amount of 200 ml, and p-toluenesulfonic acid in the amount of 1.24 g (6.40 mmol) were combined in a flask fitted with a condenser, Dean-Stark trap, and argon inlet. The mixture was heated to reflux for 18 h. The cooled mixture was concentrated by rotary evaporation and then stripped by Kugelrohr distillation to remove excess alcohol. Purity of the product was determined by thin layer chromatography and the structure confirmed by 1H and 13C NMR. fitted with a condenser The mixture was heated to reflux for 18 h The cooled mixture was concentrated by rotary evaporation stripped by Kugelrohr distillation to remove excess alcohol

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

Procedure: 9-Decen-1-ol (25.0 g, 160 mmol) was dissolved in a solution made up of t-butanol (100 ml), acetone (90 ml) and water (10 ml). To this solution was added trimethylamine-N-oxide (26.6 g, 240 mmol) and 2 ml of a solution of osmium tetroxide (500 mg) in t-butanol (25 ml). The resulting solution was stirred 20 hours under nitrogen then 10% sodium bisulfite was added (50 ml). The mixture was concentrated, then taken up in trichloromethane and washed 2 times with water, dried with Na2SO4 and concentrated to give 1,2,10-decanetriol as an oil. This material was used without further purification in preparation of the corresponding acetonide (of formula 21). The mixture was concentrated washed 2 times with water dried with Na2SO4 concentrated

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

Procedure: To 26.0 g of 9-decene-1-ol was added 10 drops of pyridine, and the mixture was placed into an eggplant flask. To the mixture was added dropwise 24.0 g of thionyl chloride, during cooling with ice. After dropping thionyl chloride, reaction was carried out for 8.5 hours at 70° C. After conclusion of the reaction, the reaction solution was diluted with dichloromethane, and then washed with an aqueous potassium carbonate. The washed solution was dried on magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography to obtain 27.7 g of 1-chloro-1-decene. (Yield: 95%) the mixture was placed into an eggplant flask during cooling with ice After conclusion of the reaction washed with an aqueous potassium carbonate The washed solution was dried on magnesium sulfate concentrated under reduced pressure The resulting residue was purified by column chromatography

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

Procedure: To 26.0 g of 9-decene-1-ol was added 10 drops of pyridine, and the mixture was placed into an eggplant flask. To the mixture was added dropwise 24.0 g of thionyl chloride, during cooling with ice. After dropping thionyl chloride, reaction was carried out for 8.5 hours at 70° C. After conclusion of the reaction, the reaction solution was diluted with dichloromethane, and then washed with an aqueous potassium carbonate. The washed solution was dried on magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography to obtain 27.7 g of 1-chloro-1-decene. (Yield: 95%) the mixture was placed into an eggplant flask during cooling with ice After conclusion of the reaction washed with an aqueous potassium carbonate The washed solution was dried on magnesium sulfate concentrated under reduced pressure The resulting residue was purified by column chromatography

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

Procedure: To a mixture of 150 g dimethyl malonate and 464 g dec-9-en-1-ol, 30 g sodium methoxide (5.4 M in methanol) was dropped in. The mixture was heated to 120° C. to and the methanol formed was distilled off. After 6 hours, the mixture was cooled down, diluted with ether and washed with HCl 2N, saturated sodium bicarbonate and water. The organic phase was dried, filtered and evaporated to dryness. The resulting yellow oil was purified by distillation to yield 258 g of a yellow oil. was dropped in formed was distilled off the mixture was cooled down diluted with ether washed with HCl 2N, saturated sodium bicarbonate and water The organic phase was dried filtered evaporated to dryness The resulting yellow oil was purified by distillation

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

Procedure: FIG. 9 shows a synthesis of 9-tetradecenyl formate, in which 5-decene is cross-metathesized with 9-decenol in the presence of Grubbs' catalyst to produce 9-tetradecenol while 1-hexene is removed from the reaction under vacuum, and in which the metathesis product, 9-tetradecenol, is reacted with formyl acetate.

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

Procedure: 9-Decen-1-ol (25.0 g, 160 mmol) was dissolved in a solution made up of t-butanol (100 ml), acetone (90 ml) and water (10 ml). To this solution was added trimethylamine-N-oxide (26.6 g, 240 mmol) and 2 ml of a solution of osmium tetroxide (50 mg) in t-butanol (25 ml). The resulting solution was stirred 20 hours under nitrogen then 10% sodium bisulfite was added (50 ml). The mixture was concentrated then taken up in trichloromethane and washed 2 times with water, dried with Na2SO4 and concentrated to give 1,2,10-decanetriol as an oil. This material was used without further purification in preparation of the corresponding acetonide (of formula 21). The mixture was concentrated washed 2 times with water dried with Na2SO4 concentrated