(3S)-3-methylpentan-1-ol

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

Procedure: 13.7 g of p-hydroxybenzoic acid and 11.4 g of (S)-(+)-3-methyl-1-pentanol were refluxed for 10 hours in toluene in the presence of sulfuric acid, while removing out the generated water from the reaction system. Subsequently, the reaction solution was washed with water to remove the sulfuric acid out. The reaction solution was then dried, concentrated, and purified by column chromatography, to obtain 17.8 g of the objective ester compound (liquid state at room temperature ([α]D23 =+7.8° (CHCl3)). (Yield: 80%) while removing out the generated water from the reaction system Subsequently, the reaction solution was washed with water to remove the sulfuric acid out The reaction solution was then dried concentrated purified by column chromatography

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

Procedure: 13.7 g of p-hydroxybenzoic acid and 11.4 g of (S)-(+)-3-methyl-1-pentanol were refluxed for 10 hours in toluene in the presence of sulfuric acid, while removing out the generated water from the reaction system. Subsequently, the reaction solution was washed with water to remove the sulfuric acid out. The reaction solution was then dried, concentrated, and purified by column chromatography, to obtain 17.8 g of the objective ester compound (liquid state at room temperature ([α]D23 =+7.8° (CHCl3)). (Yield: 80%) while removing out the generated water from the reaction system Subsequently, the reaction solution was washed with water to remove the sulfuric acid out The reaction solution was then dried concentrated purified by column chromatography

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

Procedure: In a flask were charged 15.89 g of (S)-3-methylpentanol and 65 ml of pyrimidine. After cooling to 0° to 50° C., 23.63 g of methanesulfonyl chloride was added thereto dropwise, and the mixture was allowed to react at the same temperature for 1 hour. The reaction mixture was extracted with diethyl ether, and the extract was washed with water and concentrated to obtain 12.14 g (46.42%) of the titled compound. After cooling to 0° to 50° C. to react at the same temperature for 1 hour The reaction mixture was extracted with diethyl ether the extract was washed with water concentrated

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

Procedure: In a flask were charged 15.89 g of (S)-3-methylpentanol and 65 ml of pyrimidine. After cooling to 0° to 50° C., 23.63 g of methanesulfonyl chloride was added thereto dropwise, and the mixture was allowed to react at the same temperature for 1 hour. The reaction mixture was extracted with diethyl ether, and the extract was washed with water and concentrated to obtain 12.14 g (46.42%) of the titled compound. After cooling to 0° to 50° C. to react at the same temperature for 1 hour The reaction mixture was extracted with diethyl ether the extract was washed with water concentrated

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

Procedure: In a flask were charged 15.89 g of (S)-3-methylpentanol and 65 ml of pyrimidine. After cooling to 0° to 50° C., 23.63 g of methanesulfonyl chloride was added thereto dropwise, and the mixture was allowed to react at the same temperature for 1 hour. The reaction mixture was extracted with diethyl ether, and the extract was washed with water and concentrated to obtain 12.14 g (46.42%) of the titled compound. After cooling to 0° to 50° C. to react at the same temperature for 1 hour The reaction mixture was extracted with diethyl ether the extract was washed with water concentrated

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

Procedure: 13.7 g of p-hydroxybenzoic acid and 11.4 g of (S)-(+)-3-methyl-1-pentanol were refluxed for 10 hours in toluene in the presence of sulfuric acid, while removing out the generated water from the reaction system. Subsequently, the reaction solution was washed with water to remove the sulfuric acid out. The reaction solution was then dried, concentrated, and purified by column chromatography, to obtain 17.8 g of the objective ester compound (liquid state at room temperature ([α]d23 =+7.8° (CHCl3)). (Yield: 80%) while removing out the generated water from the reaction system Subsequently, the reaction solution was washed with water to remove the sulfuric acid out The reaction solution was then dried concentrated purified by column chromatography

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

Procedure: 13.7 g of p-hydroxybenzoic acid and 11.4 g of (S)-(+)-3-methyl-1-pentanol were refluxed for 10 hours in toluene in the presence of sulfuric acid, while removing out the generated water from the reaction system. Subsequently, the reaction solution was washed with water to remove the sulfuric acid out. The reaction solution was then dried, concentrated, and purified by column chromatography, to obtain 17.8 g of the objective ester compound (liquid state at room temperature ([α]D23 =+7.8° (CHCl3)). (Yield: 80%) while removing out the generated water from the reaction system Subsequently, the reaction solution was washed with water to remove the sulfuric acid out The reaction solution was then dried concentrated purified by column chromatography