2-[2-(diethylamino)ethoxy]ethanol

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

Procedure: The same operation as in Example 1-1 or 1-2 was carried out using trans-2-decenoic acid and 2-(2-(diethylamino)ethoxy)ethanol as starting materials to give the aimed compound.

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

Procedure: The same operation as in Example 1-1 or 1-2 was carried out using trans-2-decenoic acid and 2-(2-(diethylamino)ethoxy)ethanol as starting materials to give the aimed compound.

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-aminoethoxy)ethanol (Aldrich 0.5 mmol) is treated with NaBH3CN (Aldrich, 200 mg, 3.0 mmol) in 50% aqueous methanol (30 mL). To this solution, acetaldehyde 95% purity (2 mL, 17 mmol) is added in one portion and the mixture is heated at 50° C. for 2 days in a flask under argon. After removal of the solvent under reduced pressure, the residue is dissolved in water, extracted with ethylacetate to give the title compound. After removal of the solvent under reduced pressure the residue is dissolved in water extracted with ethylacetate

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

Procedure: A modification of the procedure described in J. Am. Chem. Soc. 76:3163 (1954) was used to obtain this compound, beginning with the dropwise addition of thionyl chloride (17.02 mL, 233.42 mmol) to a solution of 2-(2-di-ethylaminoethoxy)-ethanol in benzene (100 mL). The reaction mixture was stirred at reflux for 1.5 hours and the volatiles were removedunder diminished pressure. The oily residue crystallized in ether, was nearly homogeneous by TLC, and was used without further purification. The HCl salt obtained in this reaction was very hygroscopic. Attempts at purification of the free base via distillation resulted in decomposition. CIMS 180 m/z (M+1), 183 m/z (M+3). to obtain this compound at reflux for 1.5 hours The oily residue crystallized in ether was used without further purification

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-aminoethoxy)ethanol (Aldrich 0.5 mmol) is treated with NaBH3CN (Aldrich, 200 mg, 3.0 mmol) in 50% aqueous methanol (30 mL). To this solution, acetaldehyde 95% purity (2 mL, 17 mmol) is added in one portion and the mixture is heated at 50° C. for 2 days in a flask under argon. After removal of the solvent under reduced pressure, the residue is dissolved in water, extracted with ethylacetate to give the title compound. After removal of the solvent under reduced pressure the residue is dissolved in water extracted with ethylacetate

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

Procedure: The same operation as in Example 1-1 or 1-2 was carried out using trans-2-decenoic acid and 2-(2-(diethylamino)ethoxy)ethanol as starting materials to give the aimed compound.