Methyl iodide → Ethyl 2-(4-cyanophenyl)propanoate

Ethyl 2-(4-cyanophenyl)acetate (4.0 g, 21.14 mmol) in tetrahydrofuran (20 mL) was added to a suspension of 60% sodium hydride (850 mg, 21.14 mmol) in tetrahydrofuran (20 mL) at 0° C. and stirred for 30 min. Methyl iodide (1.36 mL, 21.14 mmol) was added at 0° C.; reaction mixture was then stirred at room temperature for 4 h. Reaction mixture quenched with saturated NH4Cl solution (20 mL), diluted with water (200 mL) and extracted with ethyl acetate (2×75 mL). The combined organic layers was washed with water (50 mL) and brine (50 mL), dried over sodium sulfate, and evaporated to get crude, which was purified by column chromatography (silica gel; 60-120 mesh); the product eluted with 10% ethyl acetate in pet ether to yield ethyl 2-(4-cyanophenyl)propanoate (3.2 g, 75%) as colorless liquid.

1. customreaction mixture
2. stirringwas then stirred at room temperature for 4 h
3. customReaction mixture
4. customquenched with saturated NH4Cl solution (20 mL)
5. additiondiluted with water (200 mL)
6. extractionextracted with ethyl acetate (2×75 mL)
7. washThe combined organic layers was washed with water (50 mL) and brine (50 mL)
8. dry with materialdried over sodium sulfate
9. customevaporated
10. customto get crude, which
11. customwas purified by column chromatography (silica gel; 60-120 mesh)
12. washthe product eluted with 10% ethyl acetate in pet ether

ORD record

ord-e134f2bf17e944dca4c4c8e48f048d77

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08937092B2