diethyl 2-heptylpropanedioate

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

Procedure: In anhydrous diethyl ether was dissolved 100 g of the obtained diethyl heptylmalonate, and the mixture was added dropwise to a solution of 28.7 g of lithium aluminum hydride dispersed in 270 ml of diethyl ether. The mixture was stirred for 15 hours. Then, to the reaction mixture was added gradually 3N hydrochloric acid to make excess lithium aluminum hydride inactive. After washing with 10% aqueous solution of sodium carbonate, then water, the resulting ether layer dried with anhydrous magnesium sulfate. After distilling ether under reduced pressure, the residue was purified by silica gel chromatography (developing solvent: hexane/ethyl acetate=4/1) and distilled under reduced pressure to give 41.2 of 2-heptyl-1,3-propanediol (yield: 6%). After washing with 10% aqueous solution of sodium carbonate water, the resulting ether layer dried with anhydrous magnesium sulfate After distilling ether under reduced pressure the residue was purified by silica gel chromatography (developing solvent: hexane/ethyl acetate=4/1) distilled under reduced pressure

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

Procedure: In anhydrous diethyl ether was dissolved 100 g of the obtained diethyl heptylmalonate, and the mixture was added dropwise to a solution of 28.7 g of lithium aluminum hydride dispersed in 270 ml of diethyl ether. The mixture was stirred for 15 hours. Then, to the reaction mixture was added gradually 3N hydrochloric acid to make excess lithium aluminum hydride inactive. After washing with 10% aqueous solution of sodium carbonate, then water, the resulting ether layer dried with anhydrous magnesium sulfate. After distilling ether under reduced pressure, the residue was purified by silica gel chromatography (developing solvent: hexane/ethyl acetate=4/1) and distilled under reduced pressure to give 41.2 of 2-heptyl-1,3-propanediol (yield: 6%). After washing with 10% aqueous solution of sodium carbonate water, the resulting ether layer dried with anhydrous magnesium sulfate After distilling ether under reduced pressure the residue was purified by silica gel chromatography (developing solvent: hexane/ethyl acetate=4/1) distilled under reduced pressure

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

Procedure: In anhydrous diethyl ether was dissolved 100 g of the obtained diethyl heptylmalonate, and the mixture was added dropwise to a solution of 28.7 g of lithium aluminum hydride dispersed in 270 ml of diethyl ether. The mixture was stirred for 15 hours. Then, to the reaction mixture was added gradually 3N hydrochloric acid to make excess lithium aluminum hydride inactive. After washing with 10% aqueous solution of sodium carbonate, then water, the resulting ether layer dried with anhydrous magnesium sulfate. After distilling ether under reduced pressure, the residue was purified by silica gel chromatography (developing solvent: hexane/ethyl acetate=4/1) and distilled under reduced pressure to give 41.2 of 2-heptyl-1,3-propanediol (yield: 6%). After washing with 10% aqueous solution of sodium carbonate water, the resulting ether layer dried with anhydrous magnesium sulfate After distilling ether under reduced pressure the residue was purified by silica gel chromatography (developing solvent: hexane/ethyl acetate=4/1) distilled under reduced pressure

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

Procedure: In anhydrous diethyl ether was dissolved 100 g of the obtained diethyl heptylmalonate, and the mixture was added dropwise to a solution of 28.7 g of lithium aluminum hydride dispersed in 270 ml of diethyl ether. The mixture was stirred for 15 hours. Then, to the reaction mixture was added gradually 3N hydrochloric acid to make excess lithium aluminum hydride inactive. After washing with 10% aqueous solution of sodium carbonate, then water, the resulting ether layer dried with anhydrous magnesium sulfate. After distilling ether under reduced pressure, the residue was purified by silica gel chromatography (developing solvent: hexane/ethyl acetate=4/1) and distilled under reduced pressure to give 41.2 of 2-heptyl-1,3-propanediol (yield: 6%). After washing with 10% aqueous solution of sodium carbonate water, the resulting ether layer dried with anhydrous magnesium sulfate After distilling ether under reduced pressure the residue was purified by silica gel chromatography (developing solvent: hexane/ethyl acetate=4/1) distilled under reduced pressure