6-methylheptan-2-ol

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

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

Procedure: Sodium hydride (60% dispersion in mineral oil, 0.83 g, 20 mmol) and dimethylformamide (70 mL) were charged to a 250 mL three necked flask fitted with thermocouple, magnetic stirrer, condenser and dropping funnel. To the reaction mixture was added dropwise over 10 minutes 6-methylheptan-2-ol (2.77 g, 21 mmol). The reaction mixture was stirred at room temperature for 90 minutes then water (10 mL) was added. The reaction mixture was poured into water (100 mL), extracted with methyltert-butyl ether (2×100 mL), the combined organic phase dried over magnesium sulphate and the solvent removed in vacuo. The pale yellow oil was chromatographed over silica gel to yield 2-{4-[(1,5-dimethylhexyl) oxy]butyl}-1,3-dioxolane as a colourless oil (1.4 g, 73% pure by GC RPA, 3.9 mmol, chemical yield 19%). fitted with thermocouple, magnetic stirrer, condenser extracted with methyltert-butyl ether (2×100 mL) the combined organic phase dried over magnesium sulphate the solvent removed in vacuo The pale yellow oil was chromatographed over silica gel

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

Procedure: A mixture of 1.27 g (9.76 mmoles) of 6-methyl-2-heptanol (purchased from Aldrich Chemical Co., Milwaukee, Wis.) and 9.26 g (42.9 mmoles) of pyridinium chlorochromate (purchased from Aldrich Chemical Co., Milwaukee, Wis.) in 35 mL of dichloromethane was stirred at room temperature for 3.5 hours. At that point, the mixture was diluted with 150 mL of ether and 200 mL of 1M aqueous sodium hydroxide. After separating the layers, the organic layer was washed in successive order with 9:1 (volume/volume) 1M aqueous sodium hydroxide: saturated brine (2×100 mL), 10% aqueous sodium chloride (1×100 mL), 3:1 (volume/volume) 2M aqueous hydrochloric acid: saturated brine (3×100 mL), saturated aqueous sodium bicarbonate (1×100 mL), and saturated brine (1×100 mL). The organic layer was then dried over anhydrous magnesium sulfate and filtered. Removal of the volatile organic solvents by evaporation at reduced pressure afforded 1.214 g (97% yield) of the named ketone. The identity and purity of this known compound were ascertained by IR and proton NMR analysis. After separating the layers the organic layer was washed in successive order with 9:1 (volume/volume) 1M aqueous sodium hydroxide The organic layer was then dried over anhydrous magnesium sulfate filtered Removal of the volatile organic solvents by evaporation at reduced pressure

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

Procedure: Sodium hydride (60% dispersion in mineral oil, 0.83 g, 20 mmol) and dimethylformamide (70 mL) were charged to a 250 mL three necked flask fitted with thermocouple, magnetic stirrer, condenser and dropping funnel. To the reaction mixture was added dropwise over 10 minutes 6-methylheptan-2-ol (2.77 g, 21 mmol). The reaction mixture was stirred at room temperature for 90 minutes then water (10 mL) was added. The reaction mixture was poured into water (100 mL), extracted with methyltert-butyl ether (2×100 mL), the combined organic phase dried over magnesium sulphate and the solvent removed in vacuo. The pale yellow oil was chromatographed over silica gel to yield 2-{4-[(1,5-dimethylhexyl) oxy]butyl}-1,3-dioxolane as a colourless oil (1.4 g, 73% pure by GC RPA, 3.9 mmol, chemical yield 19%). fitted with thermocouple, magnetic stirrer, condenser extracted with methyltert-butyl ether (2×100 mL) the combined organic phase dried over magnesium sulphate the solvent removed in vacuo The pale yellow oil was chromatographed over silica gel

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

Procedure: Sodium hydride (60% dispersion in mineral oil, 0.83 g, 20 mmol) and dimethylformamide (70 mL) were charged to a 250 mL three necked flask fitted with thermocouple, magnetic stirrer, condenser and dropping funnel. To the reaction mixture was added dropwise over 10 minutes 6-methylheptan-2-ol (2.77 g, 21 mmol). The reaction mixture was stirred at room temperature for 90 minutes then water (10 mL) was added. The reaction mixture was poured into water (100 mL), extracted with methyltert-butyl ether (2×100 mL), the combined organic phase dried over magnesium sulphate and the solvent removed in vacuo. The pale yellow oil was chromatographed over silica gel to yield 2-{4-[(1,5-dimethylhexyl) oxy]butyl}-1,3-dioxolane as a colourless oil (1.4 g, 73% pure by GC RPA, 3.9 mmol, chemical yield 19%). fitted with thermocouple, magnetic stirrer, condenser extracted with methyltert-butyl ether (2×100 mL) the combined organic phase dried over magnesium sulphate the solvent removed in vacuo The pale yellow oil was chromatographed over silica gel

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

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

Procedure: A mixture of 1.27 g (9.76 mmoles) of 6-methyl-2-heptanol (purchased from Aldrich Chemical Co., Milwaukee, Wis.) and 9.26 g (42.9 mmoles) of pyridinium chlorochromate (purchased from Aldrich Chemical Co., Milwaukee, Wis.) in 35 mL of dichloromethane was stirred at room temperature for 3.5 hours. At that point, the mixture was diluted with 150 mL of ether and 200 mL of 1M aqueous sodium hydroxide. After separating the layers, the organic layer was washed in successive order with 9:1 (volume/volume) 1M aqueous sodium hydroxide: saturated brine (2×100 mL), 10% aqueous sodium chloride (1×100 mL), 3:1 (volume/volume) 2M aqueous hydrochloric acid: saturated brine (3×100 mL), saturated aqueous sodium bicarbonate (1×100 mL), and saturated brine (1×100 mL). The organic layer was then dried over anhydrous magnesium sulfate and filtered. Removal of the volatile organic solvents by evaporation at reduced pressure afforded 1.214 g (97% yield) of the named ketone. The identity and purity of this known compound were ascertained by IR and proton NMR analysis. After separating the layers the organic layer was washed in successive order with 9:1 (volume/volume) 1M aqueous sodium hydroxide The organic layer was then dried over anhydrous magnesium sulfate filtered Removal of the volatile organic solvents by evaporation at reduced pressure

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

Procedure: Sodium hydride (60% dispersion in mineral oil, 0.83 g, 20 mmol) and dimethylformamide (70 mL) were charged to a 250 mL three necked flask fitted with thermocouple, magnetic stirrer, condenser and dropping funnel. To the reaction mixture was added dropwise over 10 minutes 6-methylheptan-2-ol (2.77 g, 21 mmol). The reaction mixture was stirred at room temperature for 90 minutes then water (10 mL) was added. The reaction mixture was poured into water (100 mL), extracted with methyltert-butyl ether (2×100 mL), the combined organic phase dried over magnesium sulphate and the solvent removed in vacuo. The pale yellow oil was chromatographed over silica gel to yield 2-{4-[(1,5-dimethylhexyl) oxy]butyl}-1,3-dioxolane as a colourless oil (1.4 g, 73% pure by GC RPA, 3.9 mmol, chemical yield 19%). fitted with thermocouple, magnetic stirrer, condenser extracted with methyltert-butyl ether (2×100 mL) the combined organic phase dried over magnesium sulphate the solvent removed in vacuo The pale yellow oil was chromatographed over silica gel