Methyl iodide → HCID 14960635, compound

Temperature

-78 °C

To a stirred solution of naphth-2-ylpropionitrile (25 mmol, 4.52 g) in dry tetrahydrofuran (250 ml) at -78° C. was added n-butyl lithium (30 mmol, 18.75 ml; 1.6M solution in hexane) dropwise over a twenty minute period. After stirring the solution for twenty minutes at -78° C. methyl iodide (30 mmol, 4.26 g) was added in one portion. The reaction mixture was stirred for twenty minutes at -78° C. and the reaction was quenched with saturated NH4Cl (35 ml). The reaction mixture was warmed to room temperature, the volatiles were removed in vacuo, the residue diluted with water (200 ml) and extracted with diethyl ether (2×250 ml). The organic phase was washed with water (250 ml), dried over MgSO4 and concentrated in vacuo. The crude product was purified by preparative high pressure liquid chromatography (SiO2 :hexane/dichloromethane) to give α-methyl-naphth-2-ylpropionitrile as a white solid (3.21 g, 66 percent of theory).

1. additionwas added in one portion
2. customthe reaction was quenched with saturated NH4Cl (35 ml)
3. temperatureThe reaction mixture was warmed to room temperature
4. customthe volatiles were removed in vacuo
5. additionthe residue diluted with water (200 ml)
6. extractionextracted with diethyl ether (2×250 ml)
7. washThe organic phase was washed with water (250 ml)
8. dry with materialdried over MgSO4
9. concentrationconcentrated in vacuo
10. customThe crude product was purified by preparative high pressure liquid chromatography (SiO2 :hexane/dichloromethane)

ORD record

ord-c6ba1425e84b4f42965726bd01831954

Source dataset

uspto-grants-1990_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04910019