Methyl 8-[2-[(2-pentylcyclopropyl)methyl]cyclopropyl]octanoate

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

Procedure: A mixture of 8-(2-((2-pentylcyclopropan-1-yl)methyl)cyclopropyl)octanoic acid methyl ester (4.89 g), 1N aqueous solution (33.4 ml) of lithium hydroxide and dioxane (33 ml) was stirred at 60° C. overnight. The mixture was poured into a mixture of ethyl acetate (EA) and a saturated aqueous solution of ammonium chloride. The separated organic layer was washed with water and dried over magnesium sulfate. After filtration, the filtrate was concentrated in vacuo. The obtained residue was purified by chromatography on silica gel (eluted with 20% EA in n-hexane). The fractions including 8-(2-((2-pentylcyclopropan-1-yl)methyl)cyclopropyl)octanoic acid were collected and concentrated in vacuo to give 8-(2-((2-pentylcyclopropan-1-yl)methyl)cyclopropyl)octanoic acid (4.01 g) as an oil. The separated organic layer was washed with water dried over magnesium sulfate After filtration the filtrate was concentrated in vacuo The obtained residue was purified by chromatography on silica gel (eluted with 20% EA in n-hexane) were collected concentrated in vacuo

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

Procedure: A mixture of 8-(2-((2-pentylcyclopropan-1-yl)methyl)cyclopropyl)octanoic acid methyl ester (4.89 g), 1N aqueous solution (33.4 ml) of lithium hydroxide and dioxane (33 ml) was stirred at 60° C. overnight. The mixture was poured into a mixture of ethyl acetate (EA) and a saturated aqueous solution of ammonium chloride. The separated organic layer was washed with water and dried over magnesium sulfate. After filtration, the filtrate was concentrated in vacuo. The obtained residue was purified by chromatography on silica gel (eluted with 20% EA in n-hexane). The fractions including 8-(2-((2-pentylcyclopropan-1-yl)methyl)cyclopropyl)octanoic acid were collected and concentrated in vacuo to give 8-(2-((2-pentylcyclopropan-1-yl)methyl)cyclopropyl)octanoic acid (4.01 g) as an oil. The separated organic layer was washed with water dried over magnesium sulfate After filtration the filtrate was concentrated in vacuo The obtained residue was purified by chromatography on silica gel (eluted with 20% EA in n-hexane) were collected concentrated in vacuo

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

Procedure: To a mixture of linoleic acid methyl ester (2.5 g) and dichloromethane (50 ml), a 0.99M solution of diethylzinc (103 ml) in n-hexane was added under a nitrogen atmosphere. The mixture was cooled in an ice-water bath (−5° C. to 0° C.) and stirred for 1 hour at this temperature. Diodomethane (16.4 ml) was added to the mixture, and the mixture was stirred at ambient temperature overnight. After evaporation in vacuo of the solvent, the reacting mixture was dissolved in a mixture of ethyl acetate (EA) and a saturated aqueous solution of ammonium chloride. The separated organic layer was washed with water and dried over magnesium sulfate. After filtration, the filtrate was concentrated in vacuo. The obtained residue was purified by chromatography on silica gel (eluted with 1% EA in n-hexane). The fractions including 8-(2-((2-pentyl-cyclopropan-1-yl)methyl)cyclopropyl)octanoic acid methyl ester were collected and concentrated in vacuo to give 8-(2-((2-pentylcyclopropan-1-yl)methyl)cyclopropyl)octanoic acid methyl ester (2.81 g) as an oil. The mixture was cooled in an ice-water bath (−5° C. to 0° C.) Diodomethane (16.4 ml) was added to the mixture the mixture was stirred at ambient temperature overnight After evaporation in vacuo of the solvent the reacting mixture was dissolved in a mixture of ethyl acetate (EA) The separated organic layer was washed with water dried over magnesium sulfate After filtration the filtrate was concentrated in vacuo The obtained residue was purified by chromatography on silica gel (eluted with 1% EA in n-hexane) were collected concentrated in vacuo

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

Procedure: To a mixture of linoleic acid methyl ester (2.5 g) and dichloromethane (50 ml), a 0.99M solution of diethylzinc (103 ml) in n-hexane was added under a nitrogen atmosphere. The mixture was cooled in an ice-water bath (−5° C. to 0° C.) and stirred for 1 hour at this temperature. Diodomethane (16.4 ml) was added to the mixture, and the mixture was stirred at ambient temperature overnight. After evaporation in vacuo of the solvent, the reacting mixture was dissolved in a mixture of ethyl acetate (EA) and a saturated aqueous solution of ammonium chloride. The separated organic layer was washed with water and dried over magnesium sulfate. After filtration, the filtrate was concentrated in vacuo. The obtained residue was purified by chromatography on silica gel (eluted with 1% EA in n-hexane). The fractions including 8-(2-((2-pentyl-cyclopropan-1-yl)methyl)cyclopropyl)octanoic acid methyl ester were collected and concentrated in vacuo to give 8-(2-((2-pentylcyclopropan-1-yl)methyl)cyclopropyl)octanoic acid methyl ester (2.81 g) as an oil. The mixture was cooled in an ice-water bath (−5° C. to 0° C.) Diodomethane (16.4 ml) was added to the mixture the mixture was stirred at ambient temperature overnight After evaporation in vacuo of the solvent the reacting mixture was dissolved in a mixture of ethyl acetate (EA) The separated organic layer was washed with water dried over magnesium sulfate After filtration the filtrate was concentrated in vacuo The obtained residue was purified by chromatography on silica gel (eluted with 1% EA in n-hexane) were collected concentrated in vacuo