Allyl bromide → Methyl 2-(prop-2-en-1-yloxy)acetate

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To a suspension of sodium hydride (1.76 g, 60% in oil, 44.0 mmol) in DMF (40 mL) cooled at 0° C. was added dropwise methyl glycolate (3.09 mL, 3.60 g, 40.0 mmol). The mixture was warmed to 25° C., stirred for 1 h and cooled down to 0° C., before allyl bromide (3.81 mL, 5.32 g, 44.0 mmol) was added dropwise. The solution was warmed to 25° C., stirred for 1 h, poured in a saturated solution of NH4Cl (100 mL) and extracted with ethyl acetate (3×50 mL). The organic phases were washed with brine (2×50 mL), dried over sodium sulfate and the concentrated. The residue was distilled in vacuo utilizing a Vigreux column to afford the ester (2.77 g, 53%) as a colorless oil (b.p. 54-55° C./2 mmHg). 1H NMR (CDCl3) δ 3.74 (s, 3H), 4.06-4.08 (m, 4H), 5.21 (d, J=10.2 Hz, 1H), 5.29 (d, J=17.2 Hz, 1H), 5.84-5.94 (m, 1H).

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