Tetrahydrofuran → Methyl 2-(benzyloxy)acetate

Participants

Reaction Steps

To a suspension of sodium hydride (60%) (3.7 g, 93.12 mmol) in tetrahydrofuran (60 mL) was added dropwise a mixture of 1H-pyrrolo[2,3-b]pyridine (391=(5 g, 42.33 mmol) and bromoacetonitrile (10 g, 84.65 mmol) dissolved in tetrahydrofuran (40 mL) at 0° C. and the reaction mixture was stirred for 30 min at same temperature, then at room temperature for 6 h (TLC, 40% ethyl acetate in hexane, Rf=0.5). After completion of the reaction, the reaction mixture was quenched with saturated ammonium chloride solution (100 mL). The tetrahydrofuran was removed, water (100 mL) was added, and the mixture was extracted with ethyl acetate (3×100 mL). The separated organic part was washed with brine (100 mL) and dried and concentrated to get a crude mass which was purified by Combi-Flash (eluted at 20% ethyl acetate in hexane) to afford pyrrolo[2,3-b]pyridin-1-yl-acetonitrile (3) (4 g, 60%) as a light brown solid.

Provenance & Evidence