heptan-2-ol

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

Procedure: 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline (50 mg) was added to toluene (5 ml), and triethylamine (0.5 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (68 mg) in methylene chloride was then added thereto, and the mixture was heated under reflux for 10 min. Next, 2-heptanol (27 mg) was added thereto, and the mixture was further stirred with heating under reflux for 3 hr. A saturated aqueous sodium bicarbonate solution was added to stop the reaction, and the reaction solution was then extracted with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order. The extract was dried over sodium sulfate and was then concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (49 mg, yield 65%). the mixture was heated under reflux to prepare a solution the mixture was heated under reflux for 10 min with heating under reflux for 3 hr the reaction the reaction solution was then extracted with chloroform by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order The extract was dried over sodium sulfate was then concentrated The residue was purified on a column

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

Procedure: 4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (50 mg) was added to toluene (5 ml), and triethylamine (0.5 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (77 mg) in methylene chloride was then added thereto, and the mixture was heated under reflux for 10 min. Next, 2-heptanol (30 mg) was added thereto, and the mixture was further stirred with heating under reflux for 3 hr. A saturated aqueous sodium bicarbonate solution was added to stop the reaction, and the reaction solution was then extracted with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order. The extract was dried over sodium sulfate and was, then concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (25 mg, yield 31%). the mixture was heated under reflux to prepare a solution the mixture was heated under reflux for 10 min with heating under reflux for 3 hr the reaction the reaction solution was then extracted with chloroform by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order The extract was dried over sodium sulfate concentrated The residue was purified on a column

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

Procedure: 4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (50 mg) was added to toluene (5 ml), and triethylamine (0.5 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (77 mg) in methylene chloride was then added thereto, and the mixture was heated under reflux for 10 min. Next, 2-heptanol (30 mg) was added thereto, and the mixture was further stirred with heating under reflux for 3 hr. A saturated aqueous sodium bicarbonate solution was added to stop the reaction, and the reaction solution was then extracted with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order. The extract was dried over sodium sulfate and was, then concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (25 mg, yield 31%). the mixture was heated under reflux to prepare a solution the mixture was heated under reflux for 10 min with heating under reflux for 3 hr the reaction the reaction solution was then extracted with chloroform by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order The extract was dried over sodium sulfate concentrated The residue was purified on a column

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

Procedure: 2-Heptanol (200 g, 1.72 mol) and cyclopropanecarboxylic acid (163 g, 1.90 mol) were added into toluene (500 mL), followed by p-toluenesulfonic acid (3.2 g, 0.0172 mol). The reaction mixture was heated to reflux for 6 hours, cooled to room temperature, and quenched with aqueous sodium bicarbonate (1 L). The reaction mixture was then washed with brine (0.5 L) and dried over sodium sulfate (50 g). The solvent was removed and the reaction mixture was distilled to provide the product cyclopropanecarboxylic acid 1-methyl-hexyl ester (253 g). The reaction mixture was heated to reflux for 6 hours quenched with aqueous sodium bicarbonate (1 L) The reaction mixture was then washed with brine (0.5 L) dried over sodium sulfate (50 g) The solvent was removed the reaction mixture was distilled

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

Procedure: 2-Heptanol (200 g, 1.72 mol) and cyclopropanecarboxylic acid (163 g, 1.90 mol) were added into toluene (500 mL), followed by p-toluenesulfonic acid (3.2 g, 0.0172 mol). The reaction mixture was heated to reflux for 6 hours, cooled to room temperature, and quenched with aqueous sodium bicarbonate (1 L). The reaction mixture was then washed with brine (0.5 L) and dried over sodium sulfate (50 g). The solvent was removed and the reaction mixture was distilled to provide the product cyclopropanecarboxylic acid 1-methyl-hexyl ester (253 g). The reaction mixture was heated to reflux for 6 hours quenched with aqueous sodium bicarbonate (1 L) The reaction mixture was then washed with brine (0.5 L) dried over sodium sulfate (50 g) The solvent was removed the reaction mixture was distilled

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5.0 g (28 mmol) of ethyl 2-pyridyloxyacetate were suspended in 100 ml of 2-heptanol, 1 ml of titanium tetraisopropoxide were added, and the mixture was stirred for 4 hours at 120° C. The excess 2-heptanol was subsequently distilled off under an oil pump vacuum, and the residue was purified by column chromatography. 6.2 g (90% of theory) of (1-methyl)hexyl 2-pyridyloxyacetate were obtained as a colorless oil. The excess 2-heptanol was subsequently distilled off under an oil pump vacuum the residue was purified by column chromatography

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

Procedure: Operating under the conditions of Example 1, 1 millimol of 2-heptanone in toluene (1 ml of a 1 M soln.) is reacted with 0.375 millimol of Ca[AlH2 (OCH2CH2OCH3)2 ]2 in toluene (1.78 ml of a 0.21 M soln.) during 30 mins at room temperature. After treating the reaction mixture according to the procedure of Example 1, the resultant toluene solution is gaschromatographically analyzed. The yield of 2-heptanol, the result of the reduction of 2-heptanone, is quantitative. After treating the reaction mixture

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

Procedure: Butyric anhydride (260 ml, Aldrich) was added to 2-heptanol (162 g, 1.4 mol, Aldrich) over a 1.5 hour period at 100-140° C. The mixture was heated to 160° for 4 hours. The reaction mixture was then cooled, washed with hot water, washed with aqueous sodium carbonate to remove butyric anhydride, dried over sodium sulfate, and then concentrated. Fractional distillation of the crude residue under vacuum provided 1-methylhexyl butyrate (85-110°/78-80 mm Hg, 85% yield), the structure of which was confirmed by mass spectroscopy, nuclear magnetic resonance spectroscopy, and infra red spectroscopy (not shown). The mixture was heated to 160° for 4 hours The reaction mixture was then cooled washed with hot water washed with aqueous sodium carbonate to remove butyric anhydride dried over sodium sulfate concentrated Fractional distillation of the crude residue under vacuum

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

Procedure: 2-Heptanol (162 g, 1.4 mol, Aldrich) and sodium acetate (16 g, Aldrich) were heated to 100° C. and then acetic anhydride (190 ml, BDH GPR) was added over a 1 hour period at 100-130° C. The mixture was heated to reflux for 3 hours. The reaction mixture was then cooled, washed with water, washed with aqueous sodium bicarbonate to neutrality, dried over sodium sulfate, and then concentrated. Fractional distillation of the crude residue under vacuum provided 1-methylhexyl acetate (107-108°/95-100 mm Hg, 67% yield), the structure of which was confirmed by mass spectroscopy, nuclear magnetic resonance spectroscopy, and infra red spectroscopy (not shown). The mixture was heated to reflux for 3 hours The reaction mixture was then cooled washed with water washed with aqueous sodium bicarbonate to neutrality dried over sodium sulfate concentrated Fractional distillation of the crude residue under vacuum

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

Procedure: Operating under the conditions of Example 1, 1 millimol of 2-heptanone in toluene (1 ml of a 1M soln.) is reacted with 0.375 millimol of Ca[AlH2 (OCH2CH2OCH3)2 ]2 in toluene (1.78 ml of a 0.21M soln.) during 30 mins. at room temperature. After treating the reaction mixture according to the procedure of Example 1, the resultant toluene solution is gaschromatographically analyzed. The yield of 2-heptanol, the result of the reduction of 2-heptanone, is quantitative. at room temperature After treating the reaction mixture

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

Procedure: 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline (50 mg) was added to toluene (5 ml), and triethylamine (0.5 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (68 mg) in methylene chloride was then added thereto, and the mixture was heated under reflux for 10 min. Next, 2-heptanol (27 mg) was added thereto, and the mixture was further stirred with heating under reflux for 3 hr. A saturated aqueous sodium bicarbonate solution was added to stop the reaction, and the reaction solution was then extracted with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order. The extract was dried over sodium sulfate and was then concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (49 mg, yield 65%). the mixture was heated under reflux to prepare a solution the mixture was heated under reflux for 10 min with heating under reflux for 3 hr the reaction the reaction solution was then extracted with chloroform by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order The extract was dried over sodium sulfate was then concentrated The residue was purified on a column

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

Procedure: 4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (50 mg) was added to toluene (5 ml), and triethylamine (0.5 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (77 mg) in methylene chloride was then added thereto, and the mixture was heated under reflux for 10 min. Next, 2-heptanol (30 mg) was added thereto, and the mixture was further stirred with heating under reflux for 3 hr. A saturated aqueous sodium bicarbonate solution was added to stop the reaction, and the reaction solution was then extracted with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order. The extract was dried over sodium sulfate and was, then concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (25 mg, yield 31%). the mixture was heated under reflux to prepare a solution the mixture was heated under reflux for 10 min with heating under reflux for 3 hr the reaction the reaction solution was then extracted with chloroform by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order The extract was dried over sodium sulfate concentrated The residue was purified on a column