3-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]prop-1-yne

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

Procedure: 1-azido-3,6,9,12-tetraoxapentadec-14-yne 6 (2.45 g, 9.53 mmol, 1 equiv.), triphenylphosphine (3.00 g, 11.4 mmol, 1.2 equiv.), and water (172 mL, 9.53 mmol, 1.0 equiv.) were dissolved in THF (30 mL) and stirred for 12 h when TLC (95:5 CH2Cl2/CH3OH) indicated completion. Reaction was concentrated and chromatographed (100% CH2Cl2 to 80:20:1 CH2Cl2/MeOH/Et3N) to yield 7 as a clear oil (1.88 g, 85% yield). IR (thin film, NaCl) 3372 (br), 3251 (s), 2868 (s), 2112 (w), 1652 (m), 1596 (m), 1459 (m), 1350 (m), 1301 (m), 1249 (m), 1100 (s), 946 (m), 681 (m) cm−1. 1H-NMR (500 MHz, CDCl3) δ 4.16 (m, 2H), 3.66-3.57 (m, 12H), 3.49 (t, 2H, J=5.3 Hz), 2.85 (t, 2H, J=5.0 Hz), 2.56 (bs, 2H), 2.41 (m, 1H). 13C NMR (125 MHz, CDCl3) δ 79.52, 74.63, 73.06, 70.45, 70.41, 70.24, 70.11, 68.96, 58.26, 41.50. HRMS (ES+) calc'd for C11H21NO4 (M+H) m/z 232.154335. Found 232.15402. Reaction was concentrated chromatographed (100% CH2Cl2 to 80:20:1 CH2Cl2/MeOH/Et3N)

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

Procedure: 1-azido-3,6,9,12-tetraoxapentadec-14-yne 6 (2.45 g, 9.53 mmol, 1 equiv.), triphenylphosphine (3.00 g, 11.4 mmol, 1.2 equiv.), and water (172 mL, 9.53 mmol, 1.0 equiv.) were dissolved in THF (30 mL) and stirred for 12 h when TLC (95:5 CH2Cl2/CH3OH) indicated completion. Reaction was concentrated and chromatographed (100% CH2Cl2 to 80:20:1 CH2Cl2/MeOH/Et3N) to yield 7 as a clear oil (1.88 g, 85% yield). IR (thin film, NaCl) 3372 (br), 3251 (s), 2868 (s), 2112 (w), 1652 (m), 1596 (m), 1459 (m), 1350 (m), 1301 (m), 1249 (m), 1100 (s), 946 (m), 681 (m) cm−1. 1H-NMR (500 MHz, CDCl3) δ 4.16 (m, 2H), 3.66-3.57 (m, 12H), 3.49 (t, 2H, J=5.3 Hz), 2.85 (t, 2H, J=5.0 Hz), 2.56 (bs, 2H), 2.41 (m, 1H). 13C NMR (125 MHz, CDCl3) δ 79.52, 74.63, 73.06, 70.45, 70.41, 70.24, 70.11, 68.96, 58.26, 41.50. HRMS (ES+) calc'd for C11H21NO4 (M+H) m/z 232.154335. Found 232.15402. Reaction was concentrated chromatographed (100% CH2Cl2 to 80:20:1 CH2Cl2/MeOH/Et3N)