Methyl iodide → HCID 14699378, compound

Temperature

-78 °C

To a stirred solution of (3-methyl-2-naphthalenyl)acetonitrile (2.17 g, 12 mmol) in dry THF (125 mL) cooled to -78° C. was added n-BuLi (8.44 mL, 13.5 mmol; 1.6M solution in hexanes)dropwise over 10 minutes. The resulting orange solution was stirred for 20 minutes at -78° C. and MeI (1.92 g, 13.5 mmol) was added in one portion. The reaction mixture was stirred at -78° C. for 1.25 hours and quenched with saturated NH4Cl (20 mL). After warming to room temperature, the volatiles were removed in vacuo and the residue was diluted with H2O (150 mL). The aqueous phase was extracted with Et2O (2×150 mL). The combined organic layers were washed with saturated NaCl (1×150 mL) and dried (MgSO4). Removal of the solvent in vacuo afforded the product as a light yellow solid (2.34 g, 100%). This material was of sufficient purity to be used as such.

1. stirringThe reaction mixture was stirred at -78° C. for 1.25 hours
2. customquenched with saturated NH4Cl (20 mL)
3. temperatureAfter warming to room temperature
4. customthe volatiles were removed in vacuo
5. additionthe residue was diluted with H2O (150 mL)
6. extractionThe aqueous phase was extracted with Et2O (2×150 mL)
7. washThe combined organic layers were washed with saturated NaCl (1×150 mL)
8. dry with materialdried (MgSO4)
9. customRemoval of the solvent in vacuo

ORD record

ord-bfebf863a5ea41a980123fce02c10918

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04895861