3-butoxypropan-1-ol

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

Procedure: 3-Butoxy propan-1-ol (3.15 g) synthesized in Reference Example 44 was dissolved in dichloromethane (80 mL), triethylamine (6.6 mL), p-toluenesulfonyl chloride (6.82 g) and 4-dimethylaminopyridine (0.29 g) were added thereto, and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, and the organic layer was separated and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=3:1) to give the title compound (4.46 g) as a colorless oil. the organic layer was separated dried over anhydrous sodium sulfate The solvent was evaporated under reduced pressure the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=3:1)

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium metal (2.13 g) was added by small portions to 1,3-propanediol (15.75 g) and 1-bromobutane (10.3 g) by reference to non-patent reference [J. Am. Chem. Soc. 249 (1939)]. After the addition, the mixture was stirred at 40° C. for 1 hr and further stirred at 60° C. for 1 hr. The precipitated inorganic compound was filtered off, and the filtrate was distilled away under reduced pressure to give the title compound (3.15 g) as a colorless oil. After the addition further stirred at 60° C. for 1 hr The precipitated inorganic compound was filtered off the filtrate was distilled away under reduced pressure

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

Procedure: 3-Butoxy propan-1-ol (3.15 g) synthesized in Reference Example 44 was dissolved in dichloromethane (80 mL), triethylamine (6.6 mL), p-toluenesulfonyl chloride (6.82 g) and 4-dimethylaminopyridine (0.29 g) were added thereto, and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, and the organic layer was separated and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=3:1) to give the title compound (4.46 g) as a colorless oil. the organic layer was separated dried over anhydrous sodium sulfate The solvent was evaporated under reduced pressure the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=3:1)

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium metal (2.13 g) was added by small portions to 1,3-propanediol (15.75 g) and 1-bromobutane (10.3 g) by reference to non-patent reference [J. Am. Chem. Soc. 249 (1939)]. After the addition, the mixture was stirred at 40° C. for 1 hr and further stirred at 60° C. for 1 hr. The precipitated inorganic compound was filtered off, and the filtrate was distilled away under reduced pressure to give the title compound (3.15 g) as a colorless oil. After the addition further stirred at 60° C. for 1 hr The precipitated inorganic compound was filtered off the filtrate was distilled away under reduced pressure