2-[2-(2-aminoethoxy)ethoxy]ethanol

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

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-(2-Amino-ethoxy)-ethoxy)-ethanol (4.25 g) and ethanol (40 mL) were charged to a 100 mL RB flask equipped with a magnetic stirrer. The mixture was stirred and heated to 70° C. 1,1,3,3-Tetramethyl-3-(3-oxiranylmethoxy-propyl)-1-(2-trimethylsilanyl-ethyl)-disiloxane (2.0 g) mixed with ethanol (10 g) was placed in an addition funnel and added dropwise to the flask. The mixture was stirred and maintained at 70° C. for an additional 4 hours. The reaction progress was monitored by NMR spectroscopy. Upon reaction completion, ethanol was removed under vacuum, and the mixture was vacuum distilled to remove impurities and excess raw material. equipped with a magnetic stirrer was placed in an addition funnel added dropwise to the flask The mixture was stirred maintained at 70° C. for an additional 4 hours was removed under vacuum distilled to remove impurities and excess raw material

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

Procedure: The amino group of 2-(2-(2-aminoethoxy)ethoxy)ethanol was protected as the trifluoroacetamide by reaction with excess of methyl trifluoroacetate to give in 98% yield. Briefly, methyl trifluoroacetate (3.20 g, 2.52 ml, 25 mmol) was added dropwise through a septum with stirring and gentle cooling to 2-(2-(2-aminoethoxy)ethoxy)ethanol (2.98 g, 20 mmol), and the mixture was sealed and left at room temperature for 24 hours. The volatiles were evaporated under membrane pump vacuum and bath temperature of 65° C. to give trifluoro-N-(2-(2-(2-hydroxyethoxy)ethoxy)ethyl)acetamide as a slightly yellowish oil which crystallized when stored in the refrigerator: 4.83 g, 98% yield. 1H NMR (DMSO-d6): δ 9.41 (t, 1H, NH), 4.57 (bs, 1H, OH), 3.55-3.28 (m, 12H, CH2); 13C NMR (DMSO-d6): δ 156.60 (q, J=36.1 Hz, CO), 115.96 (q, J=116 Hz, CF3), 73.15, 70.50, 70.46, 68.67, 61.08, 39.99. to give in 98% yield the mixture was sealed The volatiles were evaporated under membrane pump vacuum and bath temperature of 65° C.

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-(2-Amino-ethoxy)-ethoxy)-ethanol (4.25 g) and ethanol (40 mL) were charged to a 100 mL RB flask equipped with a magnetic stirrer. The mixture was stirred and heated to 70° C. 1,1,3,3-Tetramethyl-3-(3-oxiranylmethoxy-propyl)-1-(2-trimethylsilanyl-ethyl)-disiloxane (2.0 g) mixed with ethanol (10 g) was placed in an addition funnel and added dropwise to the flask. The mixture was stirred and maintained at 70° C. for an additional 4 hours. The reaction progress was monitored by NMR spectroscopy. Upon reaction completion, ethanol was removed under vacuum, and the mixture was vacuum distilled to remove impurities and excess raw material. equipped with a magnetic stirrer was placed in an addition funnel added dropwise to the flask The mixture was stirred maintained at 70° C. for an additional 4 hours was removed under vacuum distilled to remove impurities and excess raw material

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-(2-Amino-ethoxy)-ethoxy)-ethanol (4.25 g) and ethanol (40 mL) were charged to a 100 mL RB flask equipped with a magnetic stirrer. The mixture was stirred and heated to 70° C. 1,1,3,3-Tetramethyl-3-(3-oxiranylmethoxy-propyl)-1-(2-trimethylsilanyl-ethyl)-disiloxane (2.0 g) mixed with ethanol (10 g) was placed in an addition funnel and added dropwise to the flask. The mixture was stirred and maintained at 70° C. for an additional 4 hours. The reaction progress was monitored by NMR spectroscopy. Upon reaction completion, ethanol was removed under vacuum, and the mixture was vacuum distilled to remove impurities and excess raw material. equipped with a magnetic stirrer was placed in an addition funnel added dropwise to the flask The mixture was stirred maintained at 70° C. for an additional 4 hours was removed under vacuum distilled to remove impurities and excess raw material

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

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-(2-Amino-ethoxy)-ethoxy)-ethanol (3.52 g) and ethanol (40 mL) were charged to a 100 mL RB flask equipped with a magnetic stirrer. The mixture was stirred and heated to 70° C. 1,5-Di(tert-butyl)-3-(oxiranylmethylpropyl)-1,1,3,5,5-Pentamethyltrisiloxane (2.0 g) mixed with ethanol (10 mL) was placed in an addition funnel and added dropwise to the flask. The mixture was stirred and maintained at 70° C. for an additional 4 hours. Reaction progress was monitored by NMR spectroscopy. Upon reaction completion, the ethanol was removed by rotary evaporation, and the mixture was distilled under vacuum to remove impurities and excess raw material. equipped with a magnetic stirrer was placed in an addition funnel added dropwise to the flask The mixture was stirred maintained at 70° C. for an additional 4 hours Reaction progress Upon reaction completion the ethanol was removed by rotary evaporation the mixture was distilled under vacuum to remove impurities and excess raw material

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-(2-Amino-ethoxy)-ethoxy)-ethanol (3.52 g) and ethanol (40 mL) were charged to a 100 mL RB flask equipped with a magnetic stirrer. The mixture was stirred and heated to 70° C. 1,5-Di(tert-butyl)-3-(oxiranylmethylpropyl)-1,1,3,5,5-Pentamethyltrisiloxane (2.0 g) mixed with ethanol (10 mL) was placed in an addition funnel and added dropwise to the flask. The mixture was stirred and maintained at 70° C. for an additional 4 hours. Reaction progress was monitored by NMR spectroscopy. Upon reaction completion, the ethanol was removed by rotary evaporation, and the mixture was distilled under vacuum to remove impurities and excess raw material. equipped with a magnetic stirrer was placed in an addition funnel added dropwise to the flask The mixture was stirred maintained at 70° C. for an additional 4 hours Reaction progress Upon reaction completion the ethanol was removed by rotary evaporation the mixture was distilled under vacuum to remove impurities and excess raw material

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

Procedure: The amino group of 2-(2-(2-aminoethoxy)ethoxy)ethanol was protected as the trifluoroacetamide by reaction with excess of methyl trifluoroacetate to give in 98% yield. Briefly, methyl trifluoroacetate (3.20 g, 2.52 ml, 25 mmol) was added dropwise through a septum with stirring and gentle cooling to 2-(2-(2-aminoethoxy)ethoxy)ethanol (2.98 g, 20 mmol), and the mixture was sealed and left at room temperature for 24 hours. The volatiles were evaporated under membrane pump vacuum and bath temperature of 65° C. to give trifluoro-N-(2-(2-(2-hydroxyethoxy)ethoxy)ethyl)acetamide as a slightly yellowish oil which crystallized when stored in the refrigerator: 4.83 g, 98% yield. 1H NMR (DMSO-d6): δ 9.41 (t, 1H, NH), 4.57 (bs, 1H, OH), 3.55-3.28 (m, 12H, CH2); 13C NMR (DMSO-d6): δ 156.60 (q, J=36.1 Hz, CO), 115.96 (q, J=116 Hz, CF3), 73.15, 70.50, 70.46, 68.67, 61.08, 39.99. to give in 98% yield the mixture was sealed The volatiles were evaporated under membrane pump vacuum and bath temperature of 65° C.

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-(2-Amino-ethoxy)-ethoxy)-ethanol (4.25 g) and ethanol (40 mL) were charged to a 100 mL RB flask equipped with a magnetic stirrer. The mixture was stirred and heated to 70° C. 1,1,3,3-Tetramethyl-3-(3-oxiranylmethoxy-propyl)-1-(2-trimethylsilanyl-ethyl)-disiloxane (2.0 g) mixed with ethanol (10 g) was placed in an addition funnel and added dropwise to the flask. The mixture was stirred and maintained at 70° C. for an additional 4 hours. The reaction progress was monitored by NMR spectroscopy. Upon reaction completion, ethanol was removed under vacuum, and the mixture was vacuum distilled to remove impurities and excess raw material. equipped with a magnetic stirrer was placed in an addition funnel added dropwise to the flask The mixture was stirred maintained at 70° C. for an additional 4 hours was removed under vacuum distilled to remove impurities and excess raw material