Propynol ethoxylate synthesis
- Product Name:Propynol ethoxylate
- CAS Number:3973-18-0
- Molecular formula:C5H8O2
- Molecular Weight:100.12
107-21-1
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Yield:3973-18-0 80%
Reaction Conditions:
Stage #1: ethylene glycolwith sodium hydride in N,N-dimethyl-formamide;mineral oil at 0; for 0.5 h;
Stage #2: propargyl bromide at 0 - 50;
Steps:
1 Step 1:
2-(prop-2-yn-1-yloxy)ethan-1-ol
To a stirred mixture of sodium hydride (60% in mineral oil, 115 mg, 2.8 mmol) in anhydrous N,N-dimethylformamide (20 ml) at 0° C. was added ethane-1,2-diol (3.9 g, 63 mmol) and stirred at 0° C. for 0.5 hour.
To the resulting mixture was added 3-bromoprop-1-yne (5.0 g, 42 mmol) at 0° C. and stirred at 50° C. overnight. TLC showed the reaction was complete.
The reaction mixture was quenched with ice water (20 ml) and partitioned between ethyl acetate (80 ml) and water (100 ml).
The organic layer was collected, and the aqueous layer was extracted with ethyl acetate (50 ml*2).
The combined organic layers were washed with brine (80 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude residue which was purified by silica gel flash chromatography (eluted with 0-20% ethyl acetate in hexane) to afford 2-(prop-2-yn-1-yloxy)ethanol (3.4 g, yield 80%) as colorless oil.
References:
US2018/125821,2018,A1 Location in patent:Paragraph 0858; 0859
![Silane, (1,1-dimethylethyl)dimethyl[2-(2-propyn-1-yloxy)ethoxy]-](/CAS/20210305/GIF/339531-56-5.gif)
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