ChemicalBook CAS DataBase List Propargyl-PEG6-azide

Propargyl-PEG6-azide synthesis

5synthesis methods

Product Name:Propargyl-PEG6-azide
CAS Number:1198080-03-3
Molecular formula:C15H27N3O6
Molecular Weight:345.4

86770-69-6
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106-96-7 Synthesis

106-96-7
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1198080-03-3
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Yield:1198080-03-3 86%

Reaction Conditions:

Stage #1: 2-(2-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethanolwith sodium hydride in N,N-dimethyl-formamide;mineral oil at 0; for 0.5 h;Inert atmosphere;
Stage #2: propargyl bromide in N,N-dimethyl-formamide;mineral oil at 0 - 20; for 1 h;Inert atmosphere;

Steps:

4 Preparation of Compound 17

Compound 16 (3.16 g, 10.3 mmol) was dissolved in N,N-dimethylformamide (21 mL), and sodium hydride (55% in oil, 494 mg, 12.3 mmol) was added at 0° C. under a nitrogen atmosphere. After 30 minutes, propargyl bromide (1.2 mL, 13.4 mmol) was added at 0° C. under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 1 hour, and then distilled water (20 mL) was added to the reaction mixture, followed by extraction with ethyl acetate (2×20 mL). The collected organic layers were washed with a saturated aqueous ammonium chloride solution (10 mL) and brine (20 mL), and then dried over anhydrous sodium sulfate. Filtration, concentration and purification by column chromatography were performed to afford Compound 17 (3.05 g, 86%). ¹H-NMR (400 MHz, CDCl₃) δ 4.20 (s, 2H), 3.69-3.66 (m, 22H), 3.39 (t, J=5.0 Hz, 2H), 2.43 (s, 1H).

References:

US2022/226496,2022,A1 Location in patent:Paragraph 0299; 0304-0305