Tetrahydrofuran → Methyl 2-(benzyloxy)acetate

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.

1. additionwas added dropwise
2. customAfter completion of the reaction
3. customthe reaction mixture was quenched with saturated ammonium chloride solution (100 mL)
4. customThe tetrahydrofuran was removed
5. additionwater (100 mL) was added
6. extractionthe mixture was extracted with ethyl acetate (3×100 mL)
7. washThe separated organic part was washed with brine (100 mL)
8. customdried
9. concentrationconcentrated
10. customto get a crude mass which
11. customwas purified by Combi-Flash (eluted at 20% ethyl acetate in hexane)

ORD record

ord-61807e42bb8e445a8018fa0b4693e54e

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045486B2