2-(2-Propyn-1-yloxy)acetic acid tert-butyl ester synthesis

Yield:339531-55-4 90%

Reaction Conditions:

with sodium hydride in tetrahydrofuran;mineral oil at 20; for 3 h;

Steps:

3 Step 3

Into a 250-mL round-bottom flask, was placed prop-2-yn-1-ol (10 g, 178.4 mmol, 1.0 equiv), tetrahydrofuran (100.0 mL), sodium hydride (6.4 g, 266.7 mmol, 0.9 equiv), and tert-butyl 2-bromoacetate (28 g, 143.6 mmol, 0.8 equiv).
The resulting solution was stirred for 3 hours at room temperature.
The reaction was then quenched by the addition of 20 mL of ammonium chloride aqueous solution.
The resulting mixture was concentrated under vacuum.
The resulting solution was extracted with ethyl acetate (30 mL*3), and the organic layers were combined and concentrated under vacuum.
This resulted in 24.0 g (90%) of tert-butyl 2-(prop-2-yn-1-yloxy)acetate as a yellow solid.

References:

US2019/300521,2019,A1 Location in patent:Paragraph 0765-0766